Benzyltrimethylammonium hydroxide → (Z)-N-(4-chlorophenethyl)-4-(4-(2-(methylsulfinyl)-2-(methylthio)vinyl)-2-(trifluoromethyl)phenoxy)benzamide

HRID 453550Notes

Reaction equation

[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:29])[C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][C:18]=3[C:25]([F:28])([F:27])[F:26])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:32][S:33]([CH2:35][S:36][CH3:37])=[O:34].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:29])[C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[C:35](\[S:33]([CH3:32])=[O:34])/[S:36][CH3:37])=[CH:19][C:18]=3[C:25]([F:26])([F:28])[F:27])=[CH:12][CH:11]=2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-(4-chlorophenethyl)-4-(4-formyl-2-(trifluoromethyl)phenoxy)benzamide (0.225 g, 0.502 mmol) in THF (5 ml) was added methylsulfinyl(methylthio)methane (0.125 g, 1.00 mmol) followed by benzyltrimethylammonium hydroxide (0.114 ml, 0.251 mmol) and the reaction was stirred at 70° C. for 1 hour. The reaction was cooled, loaded onto a silica gel samplet and the product was eluted using a gradient of 0.5% methanol/dichloromethane to 15% methanol/dichloromethane. Isolated (Z)—N-(4-chlorophenethyl)-4-(4-(2-(methylsulfinyl)-2-(methylthio)vinyl)-2-(trifluoromethyl)phenoxy)benzamide (0.220 g, 79.0% yield) which by TLC appeared to be a 4:1 mixture of olefin isomers. The crude material was used directly in the next step.

Workup

temperatureThe reaction was cooled
washthe product was eluted

Sources & evidence

ORD record: ord-203504b3a42d4a4f95a96b0618f7e317
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492437B2

Reaction notes

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