Sulfuric Acid → HCID 18919193, compound

HRID 1291270Notes

Reaction equation

HRID 1291270 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]([C:21]([O:23]CC)=O)=[C:19]([CH:26]=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:6]=[CH:7][C:8]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH2:15][N:16]3[C:20]4[C:21](=[O:23])[N:2]([CH3:1])[N:3]=[CH:26][C:19]=4[N:18]=[CH:17]3)=[CH:28][CH:29]=2)=[O:10])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 6061MethylhydrazineHCID 18918968HCID 18918968, compound

Product 1

HCID 18919193HCID 18919193, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methylhydrazine (209 mg) and ethyl 1-[4-(4-chlorobenzoyl)benzyl]-4-formylimidazole-5-carboxylate (6.01 g) in ethanol (10 ml) was refluxed for 2.5 hours. After cooling to room temperature, concentrated sulfuric acid (0.1 ml) was added and the mixture was further refluxed for 15 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; n-hexane: ethyl acetate=2:1) to provide the title compound as white powder (115 mg, yield 20%). H-NMR (CDCl3) δ: 3.88(3H,s), 5.81(2H,s), 7.46(4H,d,J=8.6Hz), 7.73(2H,d,J=8.6Hz), 7.77(2H,d,J=8.6Hz), 7.97(1H,s), 8.33(1H,s).

Workup

  1. temperaturethe mixture was further refluxed for 15 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; n-hexane: ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b1afd9be50dc4d1198c735f4cc55bc9e
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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