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

HRID 453519

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:26])[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[Br:25])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[OH-].C[N+](C)(C)CC1C=CC=CC=1.[CH3:41][S:42]([CH2:44][S:45][CH3:46])=[O:43]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:26])[C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[C:44](\[S:42]([CH3:41])=[O:43])/[S:45][CH3:46])=[CH:19][C:18]=3[Br:25])=[CH:14][CH:15]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-(4-chlorophenethyl)-4-(2-bromo-4-formylphenoxy)benzamide (1.6 g, 3.5 mmol) was diluted with THF (10 mL) followed by the addition of N,N,N-trimethyl(phenyl)methanaminium hydroxide (0.79 ml, 1.7 mmol) and methylsulfinyl (methylthio)methane (0.87 g, 7.0 mmol). The reaction was stirred at 70° C. for 2 hours. The reaction mixture was loaded directly onto a silica gel column and eluted with DCM:MeOH (98:2) to yield (Z)—N-(4-chlorophenethyl)-4-(2-bromo-4-(2-(methylsulfinyl)-2-(methylthio) vinyl)phenoxy)benzamide (1.9 g, 96% yield).

Workup

washeluted with DCM:MeOH (98:2)

Sources & evidence

ORD record: ord-558783616cce47f3bf0a9cc5418151ff
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492437B2

Linked notes

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