Acetic Anhydride → N,3-bis-(4-chlorophenyl)-4-dimethylcarbamoyl-4-methyl-N-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 978171Notes

Reaction equation

HRID 978171 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][C:16]([C:19](=[O:23])[N:20]([CH3:22])[CH3:21])([CH3:18])[C:15]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1.[H][H].[C:33](OC(=O)C)(=[O:35])[CH3:34]>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:33](=[O:35])[CH3:34])[C:11]([N:13]2[CH2:17][C:16]([C:19](=[O:23])[N:20]([CH3:22])[CH3:21])([CH3:18])[C:15]([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 13825589N,3-bis-(4-chlorophenyl)-4-dimethylcarbamoyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 53786372N,3-bis-(4-chlorophenyl)-4-dimethylcarbamoyl-4-methyl-N-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 50 ml round bottomed flask was placed 0.45 g of 60% sodium hydride (0.011 mole). The sodium hydride was washed twice with hexane and suspended in 15 ml of tetrahydrofuran. A solution of 2.0 g (0.005 mole) of N,3-bis-(4-chlorophenyl)-4-dimethylcarbamoyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide in 5 ml of tetrahydrofuran was added slowly. When hydrogen evolution ceased, 1 ml of acetic anhydride was added and the mixture was stirred for 5 minutes. The reaction was partitioned between ethyl ether and brine, dried, concentrated, and chromatographed yielding 1.6 g of N,3-bis-(4-chlorophenyl)-4-dimethylcarbamoyl-4-methyl-N-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide, an oil. NMR and IR data were consistent with the structure.

Workup

  1. customIn a 50 ml round bottomed flask was placed
  2. washThe sodium hydride was washed twice with hexane
  3. customThe reaction was partitioned between ethyl ether and brine
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-1a954d2aff614ae7812c308ef01ffec3
Source dataset
uspto-grants-1987_05
Patent number
US04663341

Reaction notes

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