{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-8bc54c6029fd40429fc5c05da891f8e6","dataset_id":"ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd","reaction_class":"Sulfonamide synthesis","transformation_sha256":"29330a1163aab3e23d3d8990b166e2349a210de78f1f09514369cdbc27216efc","doi":"10.1021/co400012m","dataset_source_slug":"ord-dataset-5eb7f2689f4a42eba63ad9e37e49a5cd","publication_source_slug":"ord-publication-fc74db030e2b9b5f","route_slugs":["ord-8bc54c6029fd40429fc5c05da891f8e6-7e2458d243b1","ord-8bc54c6029fd40429fc5c05da891f8e6-0a3c341b6bac"],"reactant_slugs":["ord-compound-f296ce257e2fac118071","ord-compound-4826e23ed48da988853b"],"product_slugs":["ord-compound-25c091f6d33ae45db9fd"],"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":{"inputs":{"amine and nahco3 in h2o/peg":{"components":[{"identifiers":[{"type":"NAME","value":"NaHCO3"},{"type":"SMILES","value":"O=C([O-])O.[Na+]"}],"amount":{"moles":{"value":0.4,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"},{"identifiers":[{"type":"NAME","value":"water"},{"type":"SMILES","value":"O"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"},{"identifiers":[{"type":"SMILES","value":"O=C(OCC1=CC=CC=C1)C2NCCC2"}],"amount":{"moles":{"value":0.22,"units":"MILLIMOLE"}},"reaction_role":"REACTANT","is_limiting":false},{"identifiers":[{"type":"NAME","value":"PEG400"},{"type":"SMILES","details":"NAME resolved by the PubChem API","value":"OCCOCCOCCOCCOCCO"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}],"flow_rate":{"value":0.25,"units":"MILLILITER_PER_MINUTE"}},"sulfonyl chloride in acetone":{"components":[{"identifiers":[{"type":"SMILES","value":"CC1=CC(C)=C(S(=O)(Cl)=O)C(C)=C1"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT","is_limiting":true},{"identifiers":[{"type":"NAME","value":"acetone"},{"type":"SMILES","value":"CC(C)=O"}],"amount":{"volume":{"value":2,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}],"flow_rate":{"value":0.25,"units":"MILLILITER_PER_MINUTE"}}},"setup":{"vessel":{"type":"TUBE","material":{"type":"PLASTIC","details":"PTFE"},"attachments":[{"type":"PRESSURE_REGULATOR","details":"back pressure regulator"}],"volume":{"value":10,"units":"MILLILITER"}}},"conditions":{"temperature":{"control":{"type":"CUSTOM","details":"\"warmed\""},"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"PRESSURIZED","details":"back pressure regulator"},"setpoint":{"value":100,"units":"PSI"}},"flow":{"type":"PLUG_FLOW_REACTOR","tubing":{"type":"PTFE"}}},"workups":[{"type":"ADDITION","input":{"components":[{"identifiers":[{"type":"NAME","value":"Et2O"},{"type":"SMILES","value":"CCOCC"}],"amount":{"volume":{"value":4,"units":"MILLILITER"}},"reaction_role":"WORKUP"},{"identifiers":[{"type":"NAME","value":"HCl"},{"type":"SMILES","value":"Cl"}],"amount":{"moles":{"value":3,"units":"MILLIMOLE"}},"reaction_role":"WORKUP"},{"identifiers":[{"type":"NAME","value":"water"},{"type":"SMILES","value":"O"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"WORKUP"}]}},{"type":"EXTRACTION","keep_phase":"organic"},{"type":"WASH","input":{"components":[{"identifiers":[{"type":"NAME","value":"water"},{"type":"SMILES","value":"O"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}}}]}},{"type":"WASH","input":{"components":[{"identifiers":[{"type":"NAME","value":"water"},{"type":"SMILES","value":"O"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"WORKUP"}]}},{"type":"DRY_WITH_MATERIAL","input":{"components":[{"identifiers":[{"type":"NAME","value":"Na2SO4"},{"type":"SMILES","value":"O=S(=O)([O-])[O-].[Na+].[Na+]"}]}]}},{"type":"CONCENTRATION"}],"outcomes":[{"reaction_time":{"value":20,"units":"MINUTE"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc1cc(C)c(S(=O)(=O)N2CCCC2C(=O)OCc2ccccc2)c(C)c1"}],"is_desired_product":true,"measurements":[{"analysis_key":"isolated weight","type":"YIELD","is_normalized":true,"percentage":{"value":76}},{"analysis_key":"crude nmr","type":"YIELD","is_normalized":true,"percentage":{"value":90}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated weight":{"type":"WEIGHT","is_of_isolated_species":true},"nmr of pure":{"type":"NMR_1H","is_of_isolated_species":true},"gcms":{"type":"GCMS","is_of_isolated_species":true},"crude nmr":{"type":"NMR_1H","details":"NMR of crude reaction mixture before workup","is_of_isolated_species":false,"instrument_manufacturer":"Bruker"}}}],"provenance":{"doi":"10.1021/co400012m","publication_url":"https://pubs.acs.org/doi/full/10.1021/co400012m"}}},"entities":[{"slug":"ord-compound-f296ce257e2fac118071","name":"C12H15NO2 · ORD VVCLBQFBKZQOAF-UHFFFAOYSA-N","smiles":"O=C(OCc1ccccc1)C1CCCN1","inchi":"InChI=1S/C12H15NO2/c14-12(11-7-4-8-13-11)15-9-10-5-2-1-3-6-10/h1-3,5-6,11,13H,4,7-9H2","formula":"C12H15NO2"},{"slug":"ord-compound-4826e23ed48da988853b","name":"C9H11ClO2S · ORD PVJZBZSCGJAWNG-UHFFFAOYSA-N","smiles":"Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1","inchi":"InChI=1S/C9H11ClO2S/c1-6-4-7(2)9(8(3)5-6)13(10,11)12/h4-5H,1-3H3","formula":"C9H11ClO2S"},{"slug":"ord-compound-25c091f6d33ae45db9fd","name":"C21H25NO4S · ORD WQZWTYRPZOFJPP-UHFFFAOYSA-N","smiles":"Cc1cc(C)c(S(=O)(=O)N2CCCC2C(=O)OCc2ccccc2)c(C)c1","inchi":"InChI=1S/C21H25NO4S/c1-15-12-16(2)20(17(3)13-15)27(24,25)22-11-7-10-19(22)21(23)26-14-18-8-5-4-6-9-18/h4-6,8-9,12-13,19H,7,10-11,14H2,1-3H3","formula":"C21H25NO4S"}],"dataset":{"dataset_id":"ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd","name":"39 compound library from \"Building a Sulfonamide Library by Eco-Friendly Flow Synthesis\"","description":"Library generated in DOI 10.1021/co400012m (Table 2)","records_in_source":39,"path":"data/5e/ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd.parquet","sha256":"2f478e163ab9f9ee2f001172fc9f0c33b0a65ec2dc787c12298f6e85bc86f7a6","bytes":11134,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/5e/ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/5e/ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd.parquet"},"publication":{"slug":"ord-publication-fc74db030e2b9b5f","title":"Literature experiment — 10.1021/co400012m","source_type":"paper","doi":"10.1021/co400012m","url":"https://doi.org/10.1021/co400012m","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"]}
