Dimethylformamide → HCID 13537980, compound

HRID 1284404Notes

Reaction equation

HRID 1284404 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:6]=[CH:5][C:4]=1[C:16]([NH2:18])=O.S(Cl)(Cl)=O.CN(C=O)C>C1(C)C=CC=CC=1>[F:20][C:2]([F:1])([F:19])[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:6]=[CH:5][C:4]=1[C:16]#[N:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1904701-(2,4-Dichlorophenyl)-5-(trifluoromethyl)-1h-pyrazole-4-carboxamide

Product 1

HCID 13537980HCID 13537980, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(Trifluoromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxamide (2.36 grams, 0.073 mole) was suspended in 30 ml of toluene, 10 ml of thionyl chloride, and about 1 ml of DMF. The suspension was stirred and heated to reflux, then refluxed for 11/2 hours. Solvent and excess thionyl chloride was removed in vacuo. The crude solid was crystallized from toluene yielding 5-(trifluoromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbonitrile, yield 0.7 gram, mp=83°-85° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturerefluxed for 11/2 hours
  4. customSolvent and excess thionyl chloride was removed in vacuo
  5. customThe crude solid was crystallized from toluene

Sources & evidence

ORD record
ord-a17069991f8c45499ada1b22a6bde433
Source dataset
uspto-grants-1986_01
Patent number
US04563210

Reaction notes

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