Hydrochloric Acid → HCID 178518626, compound

HRID 1370110Notes

Reaction equation

HRID 1370110 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)=[O:21].[OH-].[Na+].Cl>C(#N)C>[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=[O:21])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 178507665HCID 178507665, compound

Product 1

HCID 178518626HCID 178518626, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-amino-4-(trans-4-hydroxycyclohexylamino)benzotrifluoride (657 mg) in acetonitrile (7 mL) was added 1,1′-carbonyldiimidazole (1.17 g), and the mixture was stirred at 60° C. under nitrogen atmosphere for 3 hours. After adding 1N-sodium hydroxide solution (5 mL), the mixture was stirred at 60° C. for an hour. The mixture was neutralized with concentrated hydrochloric acid at 0° C. The resulting precipitate was collected by filtration and washed successively with water and diethyl ether to give 1-(trans-4-hydroxycyclohexyl)-5-trifluoromethyl-2,3-dihydro-1H-benzimidazol-2-one (549.5 mg) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at 60° C. for an hour
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed successively with water and diethyl ether

Sources & evidence

ORD record
ord-500357ec4c4a4bc3abdc76757d274307
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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