Sodium Chloride → HCID 9886519, compound

HRID 840745Notes

Reaction equation

HRID 840745 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 amino, 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-505d2099be854a4e8b6adfce476e7c90
Source dataset
uspto-grants-2002_04
Patent number
US06369091B1

Reaction notes

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