Sodium Chloride → HCID 9886519, compound

HRID 1072541Notes

Reaction equation

HRID 1072541 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:27]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[Cl-].[Na+]>C1COCC1.O>[CH:27]1([C:33]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:9][C:10]4[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:11]=4[N:12]=3)=[CH:4][CH:3]=2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 75938Cyclohexanecarbonyl chlorideHCID 22387246HCID 22387246, compound

Product 1

HCID 9886519HCID 9886519, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(N-Cyclohexanecarbonyl-4-aminophenyl)-5-trifluoromethyl benzimidazole was prepared from the amine, 2-(4-aminophenyl)-5-trifluoromethyl benzimidazole (1.2 see above). The amine (0.239 g, 0.86-mmol) was dissolved in THF:H2O (5 ml, 1:1) followed by K2CO3 (0.1213 g, 0.88 mmol) and cyclohexyl carbonyl chloride (130 μL, 0.95 mmol). The reaction mixture was shaken for 23 h at room temperature. Sodium chloride was added to the reaction and the mixture extracted with EtOAc. The combined organic extracts were washed with water, dried over Na2SO4 and concentrated under vacuum. The resulting solid was purified by preparative TLC (10% MeOH in CH2Cl2).

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe resulting solid was purified by preparative TLC (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6eb68206ab8c4dd9aa533ee492d5174b
Source dataset
uspto-grants-2005_06
Patent number
US06911462B2

Reaction notes

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