4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86625553, compound

HRID 70933Notes

Reaction equation

HRID 70933 reaction equation
[NH2:1][C:2]([CH3:23])([CH2:5][N:6]1[N:10]=[C:9]2[CH:11]=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:8]2=[N:7]1)[C:3]#[N:4].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[S:31])=[CH:28][CH:27]=1>>[F:18][C:15]([F:16])([F:17])[C:14]1[C:8]2[C:9](=[N:10][N:6]([CH2:5][C:2]([NH:1][C:30](=[S:31])[C:29]3[CH:28]=[CH:27][C:26]([C:25]([F:24])([F:35])[F:36])=[CH:34][CH:33]=3)([C:3]#[N:4])[CH3:23])[N:7]=2)[CH:11]=[C:12]([C:19]([F:21])([F:20])[F:22])[CH:13]=1

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 86625552HCID 86625552, compound

Product 1

HCID 86625553HCID 86625553, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(4,6-bis(trifluoromethyl)-2H-benzotriazol-2-yl)-2-methylpropionitrile, described in Example 23, and 4-trifluoromethylthiobenzoyl chloride, the title compound was isolated as a white solid (0.40 g, 83%). Rf=0.7 (1:1 EA/heptane). MS (ES): M/Z [M+H]=542. 1H NMR: (400 MHz, DMSO-d6): 1.79 (s, 3H), 5.62 (dd, J=60.6, 13.3 Hz, 2H), 7.76-7.97 (m, 4H), 8.13 (s, 1H), 8.92 (s, 1H) and 8.97 (s, 1H). 19F NMR (376 MHz, DMSO-d6): −61.62 (s, 3F), −61.04 (s, 3F) and −42.10 (s, 3F).

Sources & evidence

ORD record
ord-234d7494093b4491a10850600e7de7ba
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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