Pyridine → HCID 15057631, compound

HRID 654021Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[F:15][C:16]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:17]=1[NH2:18].N1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:12])(=[O:11])[NH:18][C:17]2[C:16]([F:15])=[CH:22][C:21]([F:23])=[CH:20][C:19]=2[F:24])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -50 °C

Procedure

2.35 g (10 mmol) of 4-chlorosulfonyl-benzoic acid methyl ester is suspended in 30 ml of dichloromethane with exclusion of moisture, the suspension is cooled to -50° C and, at this temperature, a solution of 1.47 g (10 mmol) of 2,4,6-trifluoroaniline and 1 ml of pyridine in 20 ml of dichloromethane is instilled. When the instillation is completed, it is allowed to come to room temperature and stirred for 12 more hours. The resulting precipitate is suctioned off and extracted with ether. The ether extract and the filtrate together are concentrated by evaporation, the residue is dissolved in dichloroethane and chromatographed on silica gel 60 (Merck) with ethyl acetate/hexane. 2.71 g (7.96 mmol)=78.6% of the theoretical yield is obtained as a partially crystalline, partially amorphous product.

Workup

customto come to room temperature
extractionextracted with ether
extractionThe ether extract
concentrationthe filtrate together are concentrated by evaporation
dissolutionthe residue is dissolved in dichloroethane
customchromatographed on silica gel 60 (Merck) with ethyl acetate/hexane
custom2.71 g (7.96 mmol)=78.6% of the theoretical yield
customis obtained as a partially crystalline, partially amorphous product

Sources & evidence

ORD record: ord-66ddaca1badd4c8da371a3e66caea453
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130119

Reaction notes

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