Hydrazinecarboxylic acid, ethyl ester → Ethyl 3-[6-(p-bromophenyl)-5-methyl-3-pyridazinyl]carbazate

HRID 372708Notes

Reaction equation

HRID 372708 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11](Cl)=[CH:10][C:9]=2[CH3:15])=[CH:4][CH:3]=1.[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[NH:17][NH2:18]>C(O)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([NH:18][NH:17][C:16]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][C:9]=2[CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 203982893-(p-Bromophenyl)-6-chloro-4-methylpyridazine

Product 1

HCID 20326503Ethyl 3-[6-(p-bromophenyl)-5-methyl-3-pyridazinyl]carbazate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 8.49 g. of 6-(p-bromophenyl)-5-methyl-3-chloropyridazine and 6.25 g. of ethyl carbazate in 100 ml. of n-butyl alcohol is prepared. This solution is stirred and heated at reflux temperature for 4 hours. The reaction mixture is cooled to room temperature and the solvent removed on a rotating evaporator. Water is added to the residue and the resulting solid filtered, washed with water, ether and dried. The product is recrystallized from ethanol to yield the product, m.p. 178°-179° C.

Workup

  1. additionA mixture of 8.49 g
  2. temperatureheated
  3. temperatureat reflux temperature for 4 hours
  4. customthe solvent removed on a rotating evaporator
  5. additionWater is added to the residue
  6. filtrationthe resulting solid filtered
  7. washwashed with water, ether
  8. customdried
  9. customThe product is recrystallized from ethanol
  10. customto yield the product, m.p. 178°-179° C.

Sources & evidence

ORD record
ord-f8433282216e4f7facc71cd93ed17452
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Reaction notes

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