Ethyl Acetate → HCID 54318896, compound
Reaction equation
[C:1]1([S:7]([NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([O-:21])=[O:20])=[N:17][CH:18]=2)=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=O)C.[CH3:28][CH2:29][CH:30](O)[CH2:31][CH3:32]>S(=O)(=O)(O)O>[C:1]1([S:7]([NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([O:21][CH:30]([CH2:31][CH3:32])[CH2:29][CH3:28])=[O:20])=[N:17][CH:18]=2)=[O:12])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
5 drops of concentrated sulfuric acid were added to 0.9 g (2.94 mmol) of 5-[((phenylsulfonyl)amino)carbonyl]-pyridine-2-carboxylate in 30 ml of 3-pentanol, while stirring, and the mixture was heated at 90° C. for 6 hours. The excess 3-pentanol was distilled off in vacuo and the residue was treated with ethyl acetate. The crystalline crude product was combined with the product obtained from the mother liquor by purification by column chromatography (melting point 186° to 187° C.), treated with hot ethyl acetate, cooled, filtered off with suction and washed with ethyl acetate. This gave 0.55 g of the colorless title compound, melting point 182° to 183° C.
Workup
- distillationThe excess 3-pentanol was distilled off in vacuo
- additionthe residue was treated with ethyl acetate
- customobtained from the mother liquor by purification by column chromatography (melting point 186° to 187° C.)
- temperaturecooled
- filtrationfiltered off with suction
- washwashed with ethyl acetate
Sources & evidence
- ORD record
- ord-6bd2cbbffc724748a70641fce04391fe
- Source dataset
- uspto-grants-1995_06
- Patent number
- US05428046
Reaction notes
Loading…