{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-065a25a8e27e42e0a91bfb691ac92afa","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"141cf8a4c83868b32dbd13037192a8289e94da1c66548054588ed1b4bc650273","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-065a25a8e27e42e0a91bfb691ac92afa-0499e4003c42","ord-065a25a8e27e42e0a91bfb691ac92afa-aa70197cdeb6"],"reactant_slugs":["ord-compound-6292cc6be07db29d963a","ord-compound-7a5ea1f0381bb40c0ab8"],"product_slugs":["ord-compound-a517714b76c8c76973f4"],"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_128"},{"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=CSC=2C=CC=CC12"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"95-16-9"}],"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 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min  to  a  stirred  solution  of  benzothiazole  1f  (108  μL,  1.0  mmol),  concentrated  H2SO4  (107  μL,  2.0  mmol),  3-iodooxetane  (368  mg,  2.0  mmol)  and  iron(II)  sulfate  heptahydrate  (80  mg,  0.3  mmol)  in  DMSO  (10  mL)  at  60  °C.  After  1-2  min  a  further  portion  of  iron(II)  sulfate  heptahydrate  (80  mg,  0.3  mmol) was added and the mixture was stirred at 60 °C for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred at 60 °C for 60  min.  After  allowing  to  cool,  the  mixture  was  poured  into  a  0.2  M  solution  of  NaOH  (30  mL)  and  Et2O  (50  mL).  The  aqueous  and  organic  layers  were  partitioned  and  the  aqueous  layer  was  extracted   - 7 -with  Et2O  (2  x  25  mL).  The  combined  organic  extracts  were  washed  with  brine  (1  x  30  mL),  dried  (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative  thin-layer  chromatography  using  EtOAc  /  hexanes  (3:7)  as  eluent  to  give  recovered  benzothiazole 1f (60 mg, 44%), and the desired product 2f (58 mg, 30%)."},"outcomes":[{"reaction_time":{"value":2,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N=1C=2C=CC=CC2SC1C3COC3"},{"type":"CAS_NUMBER","value":"1180653-65-9"}],"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":30}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz; CDCl3) δ8.03 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.51-7.47 (m, 1H), 7.41-7.38 (m, 1H), 5.13 (dd, J = 8.3,  6.1  Hz,  2H),  5.04  (t,  J  =  6.4  Hz,  2H),  4.74-4.66  (m,  1H);  13C  NMR  (100  MHz;  CDCl3) δ  170.7,  153.3, 135.0, 126.4, 125.3, 123.1, 121.9, 76.9, 39.4"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"MS of product_1":{"type":"MS","details":"192.4","data":{"found":{"float_value":192.4,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-6292cc6be07db29d963a","name":"C7H5NS · ORD IOJUPLGTWVMSFF-UHFFFAOYSA-N","smiles":"c1ccc2scnc2c1","inchi":"InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H","formula":"C7H5NS"},{"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-a517714b76c8c76973f4","name":"C10H9NOS · ORD RXGAKSUSOSNZKH-UHFFFAOYSA-N","smiles":"c1ccc2sc(C3COC3)nc2c1","inchi":"InChI=1S/C10H9NOS/c1-2-4-9-8(3-1)11-10(13-9)7-5-12-6-7/h1-4,7H,5-6H2","formula":"C10H9NOS"}],"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"]}