{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-05d160f1b7da441183b9fa501f445612","dataset_id":"ord_dataset-5eb7f2689f4a42eba63ad9e37e49a5cd","reaction_class":"Sulfonamide synthesis","transformation_sha256":"a77cde167faf7ef7e3273f74bdf9e76ac055752ab1d916c24de98410e440b047","doi":"10.1021/co400012m","dataset_source_slug":"ord-dataset-5eb7f2689f4a42eba63ad9e37e49a5cd","publication_source_slug":"ord-publication-fc74db030e2b9b5f","route_slugs":["ord-05d160f1b7da441183b9fa501f445612-f7706a3186f7","ord-05d160f1b7da441183b9fa501f445612-204004e1ea49"],"reactant_slugs":["ord-compound-8ead36e7fd8a15b5bf27","ord-compound-4826e23ed48da988853b"],"product_slugs":["ord-compound-bc99ecf02475800f25c6"],"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":"C12=CC=CC=C1CCCN2"}],"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)N2CCCc3ccccc32)c(C)c1"}],"is_desired_product":true,"measurements":[{"analysis_key":"isolated weight","type":"YIELD","is_normalized":true,"percentage":{"value":71}},{"analysis_key":"crude nmr","type":"YIELD","is_normalized":true,"percentage":{"value":86}}],"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-8ead36e7fd8a15b5bf27","name":"C9H11N · ORD LBUJPTNKIBCYBY-UHFFFAOYSA-N","smiles":"c1ccc2c(c1)CCCN2","inchi":"InChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2","formula":"C9H11N"},{"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-bc99ecf02475800f25c6","name":"C18H21NO2S · ORD YDUJUUVGZIPXJO-UHFFFAOYSA-N","smiles":"Cc1cc(C)c(S(=O)(=O)N2CCCc3ccccc32)c(C)c1","inchi":"InChI=1S/C18H21NO2S/c1-13-11-14(2)18(15(3)12-13)22(20,21)19-10-6-8-16-7-4-5-9-17(16)19/h4-5,7,9,11-12H,6,8,10H2,1-3H3","formula":"C18H21NO2S"}],"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"]}
