Hydrazine hydrate (1:1) → HCID 69960177, compound

HRID 1291206Notes

Reaction equation

HRID 1291206 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:17]([C:18](OC)=[O:19])=[C:16]([C:22](OC)=[O:23])[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.O.[NH2:31][NH2:32]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][N:13]3[C:17]4[C:18](=[O:19])[NH:31][NH:32][C:22](=[O:23])[C:16]=4[N:15]=[CH:14]3)=[CH:26][CH:27]=2)=[O:7])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18918900HCID 18918900, compound

Product 1

HCID 69960177HCID 69960177, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[4-(4-chlorobenzoyl)benzyl]-4,5-dimethoxycarbonylimidazole (3.31 g) in methanol (20 ml) was added hydrazine monohydrate (1.68 g) and the mixture was refluxed for 5 hours. The resulting crystals were harvested by filtration and suspended in water (100 ml) and, after addition of concentrated HCl (10 ml), the suspension was stirred at 80° C. for 30 minutes. The resulting crystals were collected by filtration and dried in vacuo to provide 2.67 g (yield 88%) of the title compound. 1H-NMR (DMSO) δ: 5.78(2H,s), 7.45-7.77(8H,m), 8.49(1H,s).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. filtrationThe resulting crystals were harvested by filtration
  3. additionafter addition of concentrated HCl (10 ml)
  4. filtrationThe resulting crystals were collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-67b3cd255c1f4f02bda0a0e229680360
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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