Water → HCID 178521574, compound

HRID 1370113Notes

Reaction equation

HRID 1370113 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:5]=[CH:6][C:7]=1[NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]1.[C:20](N1C=CN=C1)(N1C=CN=C1)=[S:21].O>CN(C)C=O>[OH:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([N:8]2[C:7]3[CH:6]=[CH:5][C:4]([C:16]([F:17])([F:18])[F:19])=[CH:3][C:2]=3[NH:1][C:20]2=[S:21])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 802641,1'-ThiocarbonyldiimidazoleHCID 178507665HCID 178507665, compound

Product 1

HCID 178521574HCID 178521574, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-4-(trans-4-hydroxycyclohexylamino)benzotrifluoride (300 mg) in N,N-dimethylformamide (3 mL) was added 1,1′-thiocarbonyldiimidazole (234 mg), and the mixture was stirred at room temperature under nitrogen atmosphere for 15 hours. Water was added to the mixture, and the resulting precipitate was collected by filtration. The obtained solid was washed successively with water and diethyl ether to give 1-(trans-4-hydroxycyclohexyl)-5-trifluoromethyl-2,3-dihydro-1H-benzimidazol-2-thione (242.8 mg) as a pale brown solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washThe obtained solid was washed successively with water and diethyl ether

Sources & evidence

ORD record
ord-b6593e2f0e46408abfc0357378fc4ec4
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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