{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-692777e0346141d795b86ad587ec5cde","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"f647acb832a2c342a4515b029abfe8dda49dab375788a02938428eab43f5264a","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-692777e0346141d795b86ad587ec5cde-36ff5a14a852","ord-692777e0346141d795b86ad587ec5cde-38607280b6da"],"reactant_slugs":["ord-compound-2fc49037fc7483cc2f84","ord-compound-7a5ea1f0381bb40c0ab8"],"product_slugs":["ord-compound-51f759d564589774212c"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lsf_lit_minisci_126"},{"type":"CUSTOM","details":"rxn_tech from SURF table","value":"alkylation"},{"type":"REACTION_TYPE","details":"alkylation minisci","value":"alkylation minisci"}],"inputs":{"additive_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)(O)O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7664-93-9"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"IC1COC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"26272-85-5"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N1=CC(=NC2=CC=CC=C12)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7251-61-8"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Fe].O=S(=O)(O)O.O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7782-63-0"}],"amount":{"moles":{"value":0.6,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OO"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7722-84-1"}],"amount":{"moles":{"value":6,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7732-18-5"}],"amount":{"volume":{"value":0.6,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"67-68-5"}],"amount":{"volume":{"value":9.4,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"notes":{"procedure_details":"H2O2  (35%  in  H2O;  0.53  mL,  6.0  mmol)  was  added  to  a  stirred  solution  of  2-methylquinoxaline  1h  (288  mg,  2.0  mmol),  concentrated  H2SO4  (107  μL,  1.0  mmol),  3-iodooxetane  (368  mg,  1.0  mmol)  and  iron(II)  sulfate  heptahydrate  (167  mg,  0.6  mmol)  in  DMSO (17 mL) at 60 °C. The mixture was stirred at 60 °C for 30 min then further H2O2 (0.53 mL, 6.0 mmol) and iron(II) sulfate heptahydrate (167 mg, 0.6 mmol) was added, and the mixture was stirred at 60 °C for 30 min. One last portion of H2O2 (0.53 mL, 6.0 mmol) and iron(II) sulfate heptahydrate (167 mg, 0.6 mmol) was added, and the mixture was stirred at 60 °C for 30 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (50 mL) and extracted with EtOAc (3 x 30 mL). The combined organic extracts were washed with brine (3 x 50 mL), dried (MgSO4), filtered and the solvent removed  under  vacuum  to  leave  a  crude  residue.  The residue was purified by column chromatography on  silica  gels  using  MeOH  /  CH2Cl2  (0:1  to  1:19)  as  eluent,  followed  by  purification  by  preparative  high-performance  liquid  chromatography  to  give  the  desired  product  2h  (94  mg,  22%)  as  a  solid"},"outcomes":[{"reaction_time":{"value":1.5,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N=1C=2C=CC=CC2N=C(C1C)C3COC3"},{"type":"CAS_NUMBER","value":"1180653-68-2"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":22}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR  (400  MHz;  CDCl3) δ 8.12-8.09  (m,  1H),  8.05-8.02  (m,  1H),  7.75-7.71  (m,  2H),  5.24  (dd,  J  =  7.1Hz,  5.8Hz,  2H),  5.12  (dd,  J  =  8.4Hz,  5.7Hz,  2H),  4.76-4.68  (m,  1H),  2.61  (s,  3H);  13C  NMR  (100  MHz;  CDCl3) δ 154.0, 152.2, 141.0, 129.8, 129.4, 129.1, 128.2, 74.7, 39.2, 22.2"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"MS of product_1":{"type":"MS","details":"201.1","data":{"found":{"float_value":201.1,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-2fc49037fc7483cc2f84","name":"C9H8N2 · ORD ALHUXMDEZNLFTA-UHFFFAOYSA-N","smiles":"Cc1cnc2ccccc2n1","inchi":"InChI=1S/C9H8N2/c1-7-6-10-8-4-2-3-5-9(8)11-7/h2-6H,1H3","formula":"C9H8N2"},{"slug":"ord-compound-7a5ea1f0381bb40c0ab8","name":"C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N","smiles":"IC1COC1","inchi":"InChI=1S/C3H5IO/c4-3-1-5-2-3/h3H,1-2H2","formula":"C3H5IO"},{"slug":"ord-compound-51f759d564589774212c","name":"C12H12N2O · ORD JBQUQIFVKBRVGK-UHFFFAOYSA-N","smiles":"Cc1nc2ccccc2nc1C1COC1","inchi":"InChI=1S/C12H12N2O/c1-8-12(9-6-15-7-9)14-11-5-3-2-4-10(11)13-8/h2-5,9H,6-7H2,1H3","formula":"C12H12N2O"}],"dataset":{"dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","name":"Minisci dataset from Roche","description":"Minisci reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":130,"path":"data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","sha256":"ebefbe9aba687f182d4f068e94be0f7fd71d1189bdb2eff2aca6fedf4d522bf3","bytes":37643,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet"},"publication":{"slug":"ord-publication-91c8bf15879e5ce2","title":"Literature experiment — 10.1021/jo9010624","source_type":"paper","doi":"10.1021/jo9010624","url":"https://doi.org/10.1021/jo9010624","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}