{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-3b08d7848aae4d6da08ad8bfcd983910","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"c92059bc34e371d5409d1a4b023344c5ef63afb9ba0d3b3a565d7e3bc1516e13","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-3b08d7848aae4d6da08ad8bfcd983910-9965a35d68c2","ord-3b08d7848aae4d6da08ad8bfcd983910-38b484164605"],"reactant_slugs":["ord-compound-b70dcba11107af9209f9","ord-compound-7a5ea1f0381bb40c0ab8"],"product_slugs":["ord-compound-bb575a36643486f0bdb0"],"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_122"},{"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":1.5,"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":1.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1N=C(OC)C=2C=CC=CC2C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"24953-56-8"}],"amount":{"moles":{"value":0.75,"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":0.45,"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":4.5,"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":0.45,"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":7.05,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"notes":{"procedure_details":"H2O2  (30%  in  H2O;  0.23  mL,  2.25  mmol)  was  added  dropwise   over   5   min   to   a   stirred   solution   of   1-methoxyphthalazine   1l   (120   mg,   0.75   mmol),   concentrated  H2SO4  (80  μL,  1.5  mmol),  3-iodooxetane  (276  mg,  1.5  mmol)  and  iron(II)  sulfate  heptahydrate  (63  mg,  0.225  mmol)  in  DMSO  (7.5  mL)  at  60  °C.  After  1-2  min  a  further  portion  of  iron(II) sulfate heptahydrate (50 mg, 0.19 mmol) was added and the mixture was stirred at 60 °C for 60 min.  Ater  allowing  to  cool,  the  mixture  was  poured  into  a  0.2  M  solution  of  NaOH  which  has  been  saturated  with  solid  NaCl  (40  mL)  and  EtOAc  (50  mL).  The  aqueous  and  organic  layers  were  partitioned  and  the  aqueous  layer  was  extracted  with  EtOAc  (1  x  30  mL).  The  combined  organic  extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc / hexanes (0:1 to 3:2) to give  the  desired  product  2l  (54  mg,  34%)  as  a  solid.  An  analytical  sample  was  triturated  with  Et2O  /  EtOAc for data purposes."},"outcomes":[{"reaction_time":{"value":1,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C1NN=C(C=2C=CC=CC12)C3COC3"},{"type":"CAS_NUMBER","value":"1180653-77-3"}],"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":34}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz; CDCl3) δ 10.66 (br. s, 1H), 8.52-8.50 (m, 1H), 7.86-7.80 (m, 2H), 7.44 (d, J = 8.3 Hz, 1H), 5.11 (app. s, 2H), 5.09 (app. s, 2H), 4.73-4.65 (m, 1H); 13C NMR (100 MHz; CDCl3) δ 160.5, 145.5, 133.9, 131.9, 129.1, 128.3, 127.6, 123.8, 74.5, 36.8"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"MS of product_1":{"type":"MS","details":"203.08","data":{"found":{"float_value":203.08,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-b70dcba11107af9209f9","name":"C9H8N2O · ORD GESPRUVYTLDFDD-UHFFFAOYSA-N","smiles":"COc1nncc2ccccc12","inchi":"InChI=1S/C9H8N2O/c1-12-9-8-5-3-2-4-7(8)6-10-11-9/h2-6H,1H3","formula":"C9H8N2O"},{"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-bb575a36643486f0bdb0","name":"C11H10N2O2 · ORD CQMFUXWOJZIWIE-UHFFFAOYSA-N","smiles":"O=c1[nH]nc(C2COC2)c2ccccc12","inchi":"InChI=1S/C11H10N2O2/c14-11-9-4-2-1-3-8(9)10(12-13-11)7-5-15-6-7/h1-4,7H,5-6H2,(H,13,14)","formula":"C11H10N2O2"}],"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"]}