Methanol → methyl 2-(4-chloro-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylate

HRID 85187Notes

Reaction equation

HRID 85187 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]([OH:19])=[O:18])[C:10]=3[N:9]=2)=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=1.CO.[C:26](Cl)(=O)C(Cl)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]([O:19][CH3:26])=[O:18])[C:10]=3[N:9]=2)=[C:4]([C:20]([F:22])([F:23])[F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 67203678HCID 67203678, compound

Product 1

HCID 67201064methyl 2-(4-chloro-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Chloro-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (54; 500 mg, 1.46 mmol) was suspended in CH2Cl2 (15 mL). Methanol (2 mL) was added to solubilize. To the reaction solution was added dropwise oxalyl chloride (130 μL, 1.46 mmol). After having stirred the reaction at room temperature overnight, the reaction was concentrated. The residue was taken up in EtOAc and washed successively with saturated NaHCO3 and then brine. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by silica gel chromatography (EtOAc/pentane) afforded methyl 2-(4-chloro-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylate as an orange solid (structure not shown) (390 mg, yield: 75%).

Workup

  1. customthe reaction at room temperature overnight
  2. concentrationthe reaction was concentrated
  3. washwashed successively with saturated NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (EtOAc/pentane)

Sources & evidence

ORD record
ord-c68573f69c7e47fba67d2e74bb47a0d6
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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