Thionyl Chloride → 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carbonyl chloride

HRID 1062425Notes

Reaction equation

HRID 1062425 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH:14]=[C:15]([C:17](O)=[O:18])[N:16]=1>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH:14]=[C:15]([C:17]([Cl:3])=[O:18])[N:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 218688042-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid

Product 1

HCID 222853742-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (0.66 mL, 9 mmol) was added to a solution of 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid (1 g, 3 mmol) in toluene (10 mL). The mixture was refluxed under argon for 1.5 h and concentrated to provide 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carbonyl chloride, which was used in the next step without purification. 1H NMR (300 MHz, CD2Cl2) δ 8.40 (s, 1H), 7.69-7.09 (m, 8H).

Workup

  1. temperatureThe mixture was refluxed under argon for 1.5 h
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-381ddc6bcae14776a03dee8b23f61bb1
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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