4-(Trifluoromethyl)benzenecarbothioyl chloride → HCID 86625561, compound

HRID 70948Notes

Reaction equation

HRID 70948 reaction equation
[NH2:1][C:2]([CH3:18])([CH2:5][N:6]1[N:10]=[C:9]2[CH:11]=[C:12]([O:16][CH3:17])[CH:13]=[C:14]([Cl:15])[C:8]2=[N:7]1)[C:3]#[N:4].[F:19][C:20]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[S:26])=[CH:23][CH:22]=1>>[Cl:15][C:14]1[C:8]2[C:9](=[N:10][N:6]([CH2:5][C:2]([NH:1][C:25](=[S:26])[C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:29][CH:28]=3)([C:3]#[N:4])[CH3:18])[N:7]=2)[CH:11]=[C:12]([O:16][CH3:17])[CH:13]=1

Participants

3

Reactant 2

HCID 198624844-(Trifluoromethyl)benzenecarbothioyl chlorideHCID 666206832-amino-3-(4-chloro-6-methoxy-2H-benzotriazol-2-yl)-2-methylpropionitrile

Product 1

HCID 86625561HCID 86625561, compound

Procedure

Using a procedure similar to that described in Example 1, except using 2-amino-3-(4-chloro-6-methoxy-2H-benzotriazol-2-yl)-2-methylpropionitrile (50 mg, described in Example 42) and 4-trifluoromethylthiobenzoyl chloride (0.04 mL), the title compound was isolated as a white solid (45 mg, 51%). MS (ES): M/Z [M+H]=470. 1H NMR: (400 MHz, DICHLOROMETHANE-d2): 1.86 (s, 3H), 3.88 (s, 3H), 5.11 (d, J=13.9 Hz, 1H), 5.36 (d, J=13.9 Hz, 1H), 7.05 (d, J=2.1 Hz, 1H), 7.20 (d, J=2.0 Hz, 1H), 7.72 (s, 1H), 7.79 (d, J=8.2 Hz, 2H) and 7.92 (d, J=8.6 Hz, 2H). 19F NMR (376 MHz, DICHLOROMETHANE-d2): −42.8 (s, 3F).

Sources & evidence

ORD record
ord-5913475489f04b3b804d4727eca37ed2
Source dataset
uspto-grants-2014_09
Patent number
US08822689B2

Reaction notes

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