4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86625556, compound

HRID 2061973Notes

Reaction equation

HRID 2061973 reaction equation
[NH2:1][C:2]([CH3:20])([CH2:5][N:6]1[N:10]=[C:9]2[CH:11]=[CH:12][C:13]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:14][C:8]2=[N:7]1)[C:3]#[N:4].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[S:28])=[CH:25][CH:24]=1>>[C:3]([C:2]([NH:1][C:27](=[S:28])[C:26]1[CH:25]=[CH:24][C:23]([C:22]([F:21])([F:32])[F:33])=[CH:31][CH:30]=1)([CH3:20])[CH2:5][N:6]1[N:10]=[C:9]2[CH:11]=[CH:12][C:13]([O:15][C:16]([F:17])([F:18])[F:19])=[CH:14][C:8]2=[N:7]1)#[N:4]

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 66620463HCID 66620463, compound

Product 1

HCID 86625556HCID 86625556, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(5-trifluoromethoxy-2H-benzotriazol-2-yl)-2-methylpropionitrile (100 mg, described in Example 30) and 4-trifluoromethylthiobenzoyl chloride (0.12 mL), the title compound was isolated as a white solid (142 mg, 83%). MS (ES): M/Z [M+H]=490. 1H NMR: (400 MHz, CHLOROFORM-d): 1.75 (s, 3H), 5.48 (d, J=13.4 Hz, 1H), 5.52 (d, J=13.3 Hz, 1H), 7.47 (d, J=10.6 Hz, 1H), 7.85-7.91 (m, 4H), 8.05 (br s, 1H), 8.12 (d, 1H, J=9.3 Hz) and 8.98 (br s, 1H). 19F NMR (376 MHz, CHLOROFORM-d): −57.43 (s, 3F) and −41.96 (s, 3F).

Sources & evidence

ORD record
ord-9cd208ff987b4077b72b7617b7601aca
Source dataset
uspto-grants-2012_10
Patent number
US08283475B2

Reaction notes

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