4-(Trifluoromethyl)benzenecarbothioyl chloride → N-[2-(2H-Benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethylthiobenzamide

HRID 70923Notes

Reaction equation

HRID 70923 reaction equation
[NH2:1][C:2]([CH3:15])([CH2:5][N:6]1[N:10]=[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]2=[N:7]1)[C:3]#[N:4].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[S:23])=[CH:20][CH:19]=1>>[N:7]1[N:6]([CH2:5][C:2]([NH:1][C:22](=[S:23])[C:21]2[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:27])[F:28])=[CH:26][CH:25]=2)([C:3]#[N:4])[CH3:15])[N:10]=[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=12

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 666203802-amino-3-(2H-benzotriazol-2-yl)-2-methylpropionitrile

Product 1

HCID 25122291N-[2-(2H-Benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethylthiobenzamide

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(2H-benzotriazol-2-yl)-2-methylpropionitrile, described in Example 5, and 4-trifluoromethylthiobenzoyl chloride, the title compound was isolated as a white solid (0.12 g, 59%). Rf=0.6 (1:1 EA/heptane). MS (ES): M/Z [M+H]=406. 1H NMR: (400 MHz, DMSO-d6): 1.75 (s, 3H), 5.39-5.50 (m, 2H), 7.46 (dd, J=6.6, 3.1 Hz, 2H), 7.85-7.95 (m, 6H) and 9.01 (s, 1H).

Sources & evidence

ORD record
ord-8c078f6580ec424ca1c0d1a26a720e33
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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