Dicyclohexylcarbodiimide → (RS)-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-chloro-2-(2-chloro-phenylsulfanyl)-phenyl]-N-methyl-propionamide

HRID 1358602Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH:3]=1.[F:18][C:19]([F:36])([F:35])[C:20]1[CH:21]=[C:22]([CH:30]([CH3:34])[C:31]([OH:33])=O)[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCCl>[F:27][C:26]([F:29])([F:28])[C:24]1[CH:23]=[C:22]([CH:30]([CH3:34])[C:31]([N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH3:9])=[O:33])[CH:21]=[C:20]([C:19]([F:18])([F:35])[F:36])[CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 142 mg (0.5 mmol) of 1-chloro-4-methylamino-3-(2-chloro-phenylsulfanyl)-benzene in 2 ml of 1,2-dichloroethane were added 172 mg (0.6 mmol) of 2-(3,5-bis-trifluoromethyl-phenyl)-propionic acid and the reaction mixture was shaken at 80° C. for 1 h. Dicyclohexyl carbodiimide (97 mg, 0.6 mmol) was added and shaking was continued overnight at the same temperature. The solvent was evaporated and the residue obtained was purified by column chromatography on silica gel to yield 56 mg (20%) of the title compound as light yellow oil.

Workup

stirringshaking
waitwas continued overnight at the same temperature
customThe solvent was evaporated
customthe residue obtained
customwas purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-d3a2f6db3723495098c58055f4daa9eb
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06596773B2

Reaction notes

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