Thionyl Chloride → 4-Chloro-5-ethyl-1H-imidazole-2-carbonyl chloride
Reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[N:7]=[C:8]([C:13]([OH:15])=O)[NH:9][C:10]=1[CH2:11][CH3:12]>>[Cl:5][C:6]1[N:7]=[C:8]([C:13]([Cl:3])=[O:15])[NH:9][C:10]=1[CH2:11][CH3:12]Participants
Conditions
- Temperature
- 85 °C
Procedure
Thionyl chloride (4 mL) was added to 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (described in Example 1c, 200 mg, 0.8 mmol), and the mixture was stirred at 85° C. for 40 minutes. Following concentration under reduced pressure, the residue was azeotropically distilled with toluene twice to obtain crude 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid chloride. 5 mL pyridine was added and then ethyl 2-(4-aminophenyl)-1,3-thiazole-5-carboxylate obtained in Example (91b) was added. The mixture was stirred at room temperature for one hour. The reaction solution was diluted with ethyl acetate. The precipitated solid was collected by filtration and washed with ethyl acetate, to obtain 214 mg of the title compound as a white solid (73%).
Workup
- concentrationconcentration under reduced pressure
- distillationthe residue was azeotropically distilled with toluene twice
Sources & evidence
- ORD record
- ord-f4542ee3b779467a9a7c2aa94f07ee22
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927588B2
Reaction notes
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