Ethyl cyanoacetate → Ethyl 3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)-2-cyanopropenoate

HRID 1599987Notes

Reaction equation

HRID 1599987 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C([O-])C.[Na+].[Cl:13][C:14]1[C:15]([C:24]2[CH:29]=[C:28]([CH:30]=O)[C:27]([Cl:32])=[CH:26][C:25]=2[Cl:33])=[N:16][N:17]([CH3:23])[C:18]=1[O:19][CH:20]([F:22])[F:21]>C(O)C>[Cl:32][C:27]1[CH:26]=[C:25]([Cl:33])[C:24]([C:15]2[C:14]([Cl:13])=[C:18]([O:19][CH:20]([F:21])[F:22])[N:17]([CH3:23])[N:16]=2)=[CH:29][C:28]=1[CH:30]=[C:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 156721724-Chloro-3-(2,4-dichloro-5-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

Product 1

HCID 57065413Ethyl 3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)-2-cyanopropenoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.4 g (21 mmol) of ethyl cyanoacetate and 0.3 g (4.2 mmol) of sodium ethanolate were added to a solution of 7.5 g (21 mmol) of 4-chloro-3-(2,4-dichloro-5-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole in 70 ml of ethanol. The mixture was stirred for 4 hours then poured into ice-water, after which the solid product was filtered off, washed with n-hexane and then dried. Yield: 4.9 g.

Workup

  1. filtrationafter which the solid product was filtered off
  2. washwashed with n-hexane
  3. customdried

Sources & evidence

ORD record
ord-b95d222fc42e44748874d76745a94f97
Source dataset
uspto-grants-1998_04
Patent number
US05744426

Reaction notes

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