Water → Ethyl 2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

HRID 1835570

Reaction equation

HRID 1835570 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=O)=[CH:8][CH:7]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=O.C[N:25]([CH3:28])C=O.[OH2:29].C([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]2[N:32]([CH:33]3[CH2:34][CH2:16][CH2:17][CH2:2][CH2:3]3)[C:35]3[CH:36]=[CH:8][C:9]([C:13]([O:22][CH2:18][CH3:19])=[O:29])=[CH:10][C:28]=3[N:25]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 219431614-(3-Bromophenoxy)benzoic acid

Product 1

HCID 9914616Ethyl 2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-(3-Bromophenoxy)benzoic acid (74 g) was dissolved in chloroform (500 ml), and oxalyl chloride (33 ml) and dimethylformamide (catalytic amount) were added. The mixture was stirred for 4 hr at room temperature. The reaction mixture was concentrated under reduced pressure and dissolved in dichloromethane (150 ml). The resulting solution was added dropwise to a solution of ethyl 3-amino-4-cyclohexylaminobenzoate (66 g) obtained in the previous step in dichloromethane (500 ml) and triethylamine (71 ml), and the mixture was stirred for 1 hr at room temperature. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Diethyl ether was added to the residue for crystallization and the crystals were collected by filtration to give the title compound (129 g, yield 95%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in dichloromethane (150 ml)
  3. additionThe resulting solution was added dropwise to a solution of ethyl 3-amino-4-cyclohexylaminobenzoate (66 g)
  4. customobtained in the previous step in dichloromethane (500 ml)
  5. extractionextracted with dichloromethane
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionDiethyl ether was added to the residue for crystallization
  10. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-d99d7828564642ea8998a1d5fa265aa4
Source dataset
uspto-grants-2004_08
Patent number
US06770666B2

Linked notes

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