1,1-Dichloroethane → 3,5-Dimethyl-1-phenyl-pyrazol-4-acetonitrile

HRID 615033Notes

Reaction equation

HRID 615033 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][C:8]([NH2:10])=O)=[C:5]([CH3:11])[N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[P].O(Cl)Cl.ClC(Cl)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:6]([CH2:7][C:8]#[N:10])=[C:5]([CH3:11])[N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 14798Sodium HydroxideHCID 205427213,5-Dimethyl-1-phenyl-pyrazol-4-acetamideHCID 178479709HCID 178479709, compound

Product 1

HCID 137928693,5-Dimethyl-1-phenyl-pyrazol-4-acetonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

6 grams 3,5-dimethyl-1-phenyl-pyrazol-4-acetamide, 2.5 grams phosphorus-oxychloride and 9 milliliters dichloroethane were mixed and stirred for 2 hours at 100° C. The reaction mixture was poured on ice, diluted by the addition of chloroform and neutralized by the addition of aqueous sodium hydroxide. The organic phase was separated, washed with water, dried and the solvent evaporated. 3,5-Dimethyl-1-phenyl-pyrazol-4-acetonitrile, melting at 69°-70° C., was obtained in a yield of 82%.

Workup

  1. additionThe reaction mixture was poured on ice
  2. customThe organic phase was separated
  3. washwashed with water
  4. customdried
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-44a9dba624bd48d2891c5160bc1fc954
Source dataset
uspto-grants-1979_03
Patent number
US04146721

Reaction notes

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