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

HRID 453530Notes

Reaction equation

[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:28])[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[CH:25]3[CH2:27][CH2:26]3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[OH-].C[N+](C)(C)CC1C=CC=CC=1.[CH3:43][S:44]([CH2:46][S:47][CH3:48])=[O:45]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:28])[C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[C:46](\[S:44]([CH3:43])=[O:45])/[S:47][CH3:48])=[CH:19][C:18]=3[CH:25]3[CH2:27][CH2:26]3)=[CH:14][CH:15]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-(4-Chlorophenethyl)-4-(2-cyclopropyl-4-formylphenoxy)benzamide (160 mg, 0.381 mmol) was diluted with THF (3 mL) followed by the addition of N,N,N-trimethyl(phenyl)methanaminium hydroxide (0.0866 ml, 0.191 mmol) and methylsulfinyl(methylthio)methane (94.7 mg, 0.762 mmol). The reaction was heated to 70° C. and stirred for 2 hours. The reaction was cooled and loaded directly onto a silica gel column, eluting with ethyl acetate to yield (Z)—N-(4-chlorophenethyl)-4-(2-cyclopropyl-4-(2-(methylsulfinyl)-2-(methylthio)vinyl)phenoxy)benzamide (100 mg, 49.9% yield).

Workup

temperatureThe reaction was cooled
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-d0027c8401b5493fbe079c2edd3f49cd
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492437B2

Reaction notes

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