4-Chlorobutyryl chloride → 5-(4-Chlorobutyramido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole

HRID 1249130Notes

Reaction equation

HRID 1249130 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[C:8]=2[Cl:15])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[Cl:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23]>C(#N)C>[Cl:18][CH2:19][CH2:20][CH2:21][C:22]([NH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[C:8]=2[Cl:15])[N:5]=[CH:4][C:3]=1[C:16]#[N:17])=[O:23]

Participants

4

Reactant 2

HCID 783704-Chlorobutyryl chloride2×HCID 30189015-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 131276425-(4-Chlorobutyramido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazoleYield 29.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (12.47 g) and 4-chlorobutyryl chloride (12.3 g) in dry acetonitrile (200 ml) was stirred and gently warmed to effect dissolution. The solution was cooled to room temperature and stirred, after 48 hours a further quantity of 4-chlorobutyryl chloride (6.15 g) was added and stirring continued for 24 hours. The solution was evaporated under reduced pressure to give an oil which was chromatographed using dichloromethane-ethyl acetate (19:1) as eluent. Evaporation of the eluate containing the fastest moving component gave 5-(4-chlorobutyramido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (5 g), m.p. 173°-174° C., after crystallisation from toluene, in the form of pale yellow crystals.

Workup

  1. temperaturegently warmed
  2. dissolutiondissolution
  3. additionwas added
  4. stirringstirring
  5. customThe solution was evaporated under reduced pressure
  6. customto give an oil which
  7. customwas chromatographed
  8. customEvaporation of the eluate
  9. additioncontaining the

Sources & evidence

ORD record
ord-44b8871891de43fa95b4101124ef8844
Source dataset
uspto-grants-1986_12
Patent number
US04629495

Reaction notes

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