{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0810a7b8e5134dada871394b3a94393d","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"fb60504fcabf7eccc93cee1f8a2d40f27c068451e58aa9a81728d2a5c7c55124","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-0810a7b8e5134dada871394b3a94393d-a7eec0fd7e33","ord-0810a7b8e5134dada871394b3a94393d-d5716d99faeb"],"reactant_slugs":["ord-compound-844c99d01eaca8862f97","ord-compound-c548c24d29328ab9f616"],"product_slugs":["ord-compound-b481da9cf33ea4916f53"],"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_110"},{"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,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)N1CC(I)C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"254454-54-1"}],"amount":{"moles":{"value":3,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N1=CN(C=2C=CC=CC12)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1632-83-3"}],"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":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"notes":{"procedure_details":"H2O2  (30%  in  H2O;  0.31  mL,  3.0  mmol)  was  added  to  a  stirred  solution  of  1-methylbenzimidazole  1g  (100  mg,  1.0  mmol),  concentrated  H2SO4  (108  μL,  1.0  mmol),  1-Boc-3-(iodo)azetidine  (566  mg,  2.0  mmol)  and  iron(II)  sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (5 mL) at room temperature. The mixture was stirred at  room  temperature  for  120  min,  then  diluted  with  EtOAc  and  saturated  NaHCO3.  The  aqueous  and  organic  layers  were  partitioned  and  the  organic  layer  was  washed  with  brine,  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 (3:7 to 7:3) as eluent to give the desired product 3f(52 mg, 17%) as a solid. "},"outcomes":[{"reaction_time":{"value":2,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)N1CC(C2=NC=3C=CC=CC3N2C)C1"},{"type":"CAS_NUMBER","value":"1180653-92-2"}],"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":17}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz; CDCl3) δ 7.71-7.67 (m, 1H), 7.24-7.16 (m, 3H), 4.31-4.26 (m,  4H),  3.96-3.89  (m,  1H),  3.58  (s,  3H),  1.37  (s,  9H);    13C  NMR  (100  MHz;  CDCl3)  156.3,  153.9,  142.4, 136.2, 122.8, 122.3, 119.7, 109.1, 79.9, 53.3, 29.8, 28.5, 26.3"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"MS of product_1":{"type":"MS","details":"288.17","data":{"found":{"float_value":288.17,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-844c99d01eaca8862f97","name":"C8H8N2 · ORD FGYADSCZTQOAFK-UHFFFAOYSA-N","smiles":"Cn1cnc2ccccc21","inchi":"InChI=1S/C8H8N2/c1-10-6-9-7-4-2-3-5-8(7)10/h2-6H,1H3","formula":"C8H8N2"},{"slug":"ord-compound-c548c24d29328ab9f616","name":"C8H14INO2 · ORD XPDIKRMPZNLBAC-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)N1CC(I)C1","inchi":"InChI=1S/C8H14INO2/c1-8(2,3)12-7(11)10-4-6(9)5-10/h6H,4-5H2,1-3H3","formula":"C8H14INO2"},{"slug":"ord-compound-b481da9cf33ea4916f53","name":"C16H21N3O2 · ORD QYKQPQSZTOJOLV-UHFFFAOYSA-N","smiles":"Cn1c(C2CN(C(=O)OC(C)(C)C)C2)nc2ccccc21","inchi":"InChI=1S/C16H21N3O2/c1-16(2,3)21-15(20)19-9-11(10-19)14-17-12-7-5-6-8-13(12)18(14)4/h5-8,11H,9-10H2,1-4H3","formula":"C16H21N3O2"}],"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"]}