[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine → HCID 22618495, compound

HRID 842149Notes

Reaction equation

HRID 842149 reaction equation
[K].[C:2]([CH:4]([C:10]#[N:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:3].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[NH:24][NH2:25]>Cl>[C:5]([C:4]1[C:2]([NH2:3])=[N:25][N:24]([C:14]2[C:13]([Cl:12])=[CH:18][C:17]([C:19]([F:20])([F:22])[F:21])=[CH:16][C:15]=2[Cl:23])[C:10]=1[NH2:11])([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 86747066HCID 86747066, compound

Product 1

HCID 22618495HCID 22618495, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl dicyanoacetate potassium salt (35.2 g) was added to a stirred suspension of 2,6-dichloro-4-trifluoromethylphenylhydrazine (49 g) in hydrochloric acid (0.9M; 220 ml) and the mixture was stirred and boiled under reflux for 18 h, then cooled to precipitate a solid which was filtered off, triturated with diethyl ether (250 ml) and dried to give an off-white solid which was recrystallized from ethyl acetate-hexane to give 4-carboethoxy-3,5-diamino-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (29.2 g), m.p. 196-197° C., in the form of an off-white solid.

Workup

  1. temperatureunder reflux for 18 h
  2. temperaturecooled
  3. customto precipitate a solid which
  4. filtrationwas filtered off
  5. customtriturated with diethyl ether (250 ml)
  6. customdried
  7. customto give an off-white solid which
  8. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-32a080dac1c84f6cae9293e2d0cd8074
Source dataset
uspto-grants-2002_04
Patent number
US06372774B1

Reaction notes

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