{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-aaa2d6dcba144711a7e3a8582de8f279","dataset_id":"ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd","reaction_class":"Sulfonamide synthesis","transformation_sha256":"9f978f50dff0fa7f8968e7146762fde71c639ebad00d9d123a1cb1fb36dd04a2","doi":"10.1021/co400012m","dataset_source_slug":"ord-dataset-5eb7f2689f4a42eba63ad9e37e49a5cd","publication_source_slug":"ord-publication-fc74db030e2b9b5f","route_slugs":["ord-aaa2d6dcba144711a7e3a8582de8f279-66771cb0a215","ord-aaa2d6dcba144711a7e3a8582de8f279-2d7789dfb38c"],"reactant_slugs":["ord-compound-0f684bfd80e46bf45d69","ord-compound-4826e23ed48da988853b"],"product_slugs":["ord-compound-c5875fe78086999da34c"],"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":"IC1=CC=C(N)C=C1"}],"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)Nc2ccc(I)cc2)c(C)c1"}],"is_desired_product":true,"measurements":[{"analysis_key":"isolated weight","type":"YIELD","is_normalized":true,"percentage":{"value":72}},{"analysis_key":"crude nmr","type":"YIELD","is_normalized":true,"percentage":{"value":98}}],"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-0f684bfd80e46bf45d69","name":"C6H6IN · ORD VLVCDUSVTXIWGW-UHFFFAOYSA-N","smiles":"Nc1ccc(I)cc1","inchi":"InChI=1S/C6H6IN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2","formula":"C6H6IN"},{"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-c5875fe78086999da34c","name":"C15H16INO2S · ORD MTLDEIMAFZWTNB-UHFFFAOYSA-N","smiles":"Cc1cc(C)c(S(=O)(=O)Nc2ccc(I)cc2)c(C)c1","inchi":"InChI=1S/C15H16INO2S/c1-10-8-11(2)15(12(3)9-10)20(18,19)17-14-6-4-13(16)5-7-14/h4-9,17H,1-3H3","formula":"C15H16INO2S"}],"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"]}
