m-Tolylisothiocyanate → N-(m-tolylcarbamothioyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide

HRID 62044

Reaction equation

[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C([Li])CCC.[N:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=1)=[C:33]=[S:34]>O1CCCC1>[C:37]1([CH3:41])[CH:38]=[CH:39][CH:40]=[C:35]([NH:32][C:33]([N:21]([C:18]2[CH:19]=[CH:20][C:15]([C:12]3[N:13]=[CH:14][N:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=4)[N:11]=3)=[CH:16][CH:17]=2)[C:22](=[O:24])[CH3:23])=[S:34])[CH:36]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide in tetrahydrofuran (1.1 mL) cooled to −78° C. was added n-butyllithium (2.5 M, 0.13 mL). The reaction was stirred for 1 hour. 1-Isothiocyanato-3-methylbenzene was added and the solution was slowly warmed to 0° C. over 1 hour. The mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified via radial chromatography using a 97:3 chloroform/methanol mixture as eluent providing the title compound as a tan solid (0.062 g, 55%).

Workup

customThe mixture was quenched with aqueous ammonium chloride
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified via radial chromatography

Sources & evidence

ORD record: ord-a1c8ac62b26b460c9c80443c7658ff7d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09445594B2

Linked notes

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