(4-bromo-2,6-dichlorophenyl)hydrazine → HCID 13118709, compound

HRID 2418122Notes

Reaction equation

HRID 2418122 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][NH2:11].C(O[CH:15]=[C:16]([C:23]#[N:24])[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])C>C(O)CCC>[NH2:24][C:23]1[N:10]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([Br:8])=[CH:5][C:4]=2[Cl:9])[N:11]=[CH:15][C:16]=1[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18]

Participants

4

Reactant 2

HCID 3816096(4-bromo-2,6-dichlorophenyl)hydrazineHCID 543446152-Propen-1-yl 2-cyano-3-ethoxy-2-propenoate

Product 1

HCID 13118709HCID 13118709, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

20.5 parts by weight of 2,6-dichloro-4-bromophenylhydrazine and 14.5 parts by weight of allyl ethoxymethylene-2-cyanoacetate in 100 parts by volume of n-butanol were refluxed for 4 hours. The butanol was evaporated off, the oily residue was dissolved in 150 parts by volume of ether, and dry halogen chloride gas was passed in, with ice-cooling. The hydrochloride which had precipitated was stirred with saturated sodium bicarbonate solution, and the precipitate was filtered off with suction and dried under reduced pressure to give 24.8 parts by weight of allyl 5-amino-1-(2,6-dichloro-4-bromophenyl)-pyrazole-4-carboxylate of melting point 85° C. (active ingredient No.6).

Workup

  1. customThe butanol was evaporated off
  2. dissolutionthe oily residue was dissolved in 150 parts by volume of ether, and dry halogen chloride gas
  3. temperaturecooling
  4. customThe hydrochloride which had precipitated
  5. filtrationthe precipitate was filtered off with suction
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-8633e0185b894ba7a562047f7edce1d6
Source dataset
uspto-grants-1984_09
Patent number
US04472192

Reaction notes

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