Pyridine → HCID 86738003, compound

HRID 1577570Notes

Reaction equation

N1C=CC=CC=1.[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:16][O:17][C:18](=[O:41])[CH:19]1[CH:24]=[C:23]([N:25]2[CH:29]=[CH:28][CH:27]=[CH:26]2)[C:22]([S:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:21]([NH2:37])[C:20]1=[S:38](=[O:40])=[O:39]>CC(C)=O.O1CCOCC1.C(Cl)Cl>[CH3:16][O:17][C:18](=[O:41])[CH:19]1[CH:24]=[C:23]([N:25]2[CH:26]=[CH:27][CH:28]=[CH:29]2)[C:22]([S:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[C:21]([NH:37][C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:20]1=[S:38](=[O:40])=[O:39]

Participants

Conditions

Temperature: 40 °C

Procedure

1.4 ml of pyridine, and a solution of 7.2 g of benzoyl chloride in 30 ml of acetone, are added to 5 g of 3-amino-4-phenylthio-5-pyrrol-1-yl-sulfonylbenzoic acid methyl ester, dissolved in 25 ml of anhydrous dioxane, and the mixture is stirred at room temperature and subsequently at 40° C. The solvent is stripped off under reduced pressure, the residue is taken up in methylene chloride and the solution is washed with dilute sodium bicarbonate solution. After drying the solution over sodium sulfate, the solvent is stripped off on a rotary evaporator and the residue is recrystallized from methanol/methylene chloride. 3-Benzoylamino-4-phenylthio-5-pyrrol-1-yl-sulfonylbenzoic acid methyl ester of melting point 210°-211° C. is obtained. Yield: 59%.

Workup

washthe solution is washed with dilute sodium bicarbonate solution
dry with materialAfter drying the solution over sodium sulfate
customthe solvent is stripped off on a rotary evaporator
customthe residue is recrystallized from methanol/methylene chloride

Sources & evidence

ORD record: ord-57fa389e768c4bda906ba4c5fae4d6df
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04288449

Reaction notes

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