Sodium hydride → HCID 18185303, compound

HRID 1358739Notes

Reaction equation

HRID 1358739 reaction equation
[F:1][C:2]([F:21])([F:20])[S:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][NH:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[F:22][C:23]([F:34])([F:33])[S:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.[H-].[Na+]>>[F:21][C:2]([F:20])([F:1])[S:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([S:24][C:23]([F:34])([F:22])[F:33])=[CH:26][CH:27]=2)[C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27778824-(Trifluoromethylthio)benzyl bromideHCID 18185288HCID 18185288, compound

Product 1

HCID 18185303HCID 18185303, compoundYield 81%

Procedure

N-(4-trifluoromethylthiobenzyl)benzamide (100 mg, 0.32 mmol) was coupled with 4-(trifluoromethylthio) benzyl bromide (91 mg, 0.34 mmol) using sodium hydride (9.2 mg, 0.38 mmol) to give 130 mg (80%) of N,N-bis(4-trifluoromethylthiobenzyl)benzamide as a yellow oil. 1HNMR (360 MHz, DMSO-d6) δ 7.65 (m, 4H), 7.31-7.47 (m, 9H), 4.57-4.66 (m, 4H). MS-EI m/z 501 [M+].

Sources & evidence

ORD record
ord-ee5b1661a964427eaa0c77055d463ee9
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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