Sulfuric Acid → HCID 18918843, compound

HRID 1291269Notes

Reaction equation

HRID 1291269 reaction equation
[CH3:1][NH:2][NH2:3].[Cl:4][C:5]1[CH:31]=[CH:30][C:8]([C:9]([C:11]2[CH:29]=[CH:28][C:14]([CH2:15][N:16]3[C:20]([CH:21]=O)=[C:19]([C:23]([O:25]CC)=O)[N:18]=[CH:17]3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.S(=O)(=O)(O)O>C(O)C.O>[Cl:4][C:5]1[CH:31]=[CH:30][C:8]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH2:15][N:16]3[C:20]4[CH:21]=[N:3][N:2]([CH3:1])[C:23](=[O:25])[C:19]=4[N:18]=[CH:17]3)=[CH:28][CH:29]=2)=[O:10])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 6061MethylhydrazineHCID 18919292HCID 18919292, compound

Product 1

HCID 18918843HCID 18918843, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methylhydrazine (472 mg) and ethyl 1-[4-(4-chlorobenzoyl)benzyl]-5-formylimidazole-4-carboxylate (1.03 g) in ethanol (20 ml) was refluxed for 3 hours. After cooling to room temperature, concentrated sulfuric acid (0.2 ml) was added and the mixture was further refluxed for 21 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developer; chloroform:methanol=19:1) to provide the title compound as white powder (66 mg, yield 7%). 1H-NMR (CDCl3) δ: 3.90(3H,s), 5.47(2H,s), 7.31(2H,d,J=8.4Hz), 7.48(2H,d,J=8.4Hz), 7.73(2H,d,J=8.4Hz), 7.81(2H,d,J=8.4Hz), 7.92(1H,s), 8.00(1H,s).

Workup

  1. temperaturethe mixture was further refluxed for 21 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (developer; chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-c36c82000af045a08b0bc62f658b16c6
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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