N,N'-Dimethylthiourea → 3-Methyl-2-methylimino-7-(4-trifluoromethylphenyl)-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol hydrobromide

HRID 1595242Notes

Reaction equation

HRID 1595242 reaction equation
[Br:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:3]1=[O:21].[CH3:22][NH:23][C:24]([NH:26][CH3:27])=[S:25]>CC(C)=O>[BrH:1].[CH3:27][N:26]1[C:3]2([OH:21])[C:4]3[CH:5]=[CH:6][CH:7]=[C:8]([C:11]4[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=4)[C:9]=3[CH2:10][CH:2]2[S:25][C:24]1=[N:23][CH3:22].[CH3:27][N:26]1[C:3]2([OH:21])[C:4]3[CH:5]=[CH:6][CH:7]=[C:8]([C:11]4[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=4)[C:9]=3[CH2:10][CH:2]2[S:25][C:24]1=[N:23][CH3:22]

Participants

5

Reactant 2

HCID 2723631N,N'-DimethylthioureaHCID 217020632-Bromo-4-(4-trifluoromethylphenyl)-1-indanone

Product 2

HCID 206385833-Methyl-2-methylimino-7-(4-trifluoromethylphenyl)-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol hydrobromideHCID 206385843-Methyl-2-methylimino-7-(4-trifluoromethylphenyl)-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

426 mg (1.2 mmol) of 2-bromo-4-(4-trifluoromethylphenyl)-1-indanone and 130.2 mg (1.25 mmol) of N, N′-dimethylthiourea are dissolved in 10 ml of acetone and stirred at room temperature for 4 h. The precipitate is filtered off with suction, washed with acetone and dried in vacuo. The hydrobrornide of 3-methyl-2-methylimino-7-(4-trifluoromethylphenyl)-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol is obtained with a melting point of 202-204° C.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. washwashed with acetone
  3. customdried in vacuo

Sources & evidence

ORD record
ord-f7d55003737644dfb9f68dee9a399a35
Source dataset
uspto-grants-2001_09
Patent number
US06288093B1

Reaction notes

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