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

HRID 1927781Notes

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. fort hour. The reaction was cooled, loaded onto a silica gel sample 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-fbc22c7600f6423ba77595adfb8100ac
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183289B2

Reaction notes

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