Triethylamine → tert-Butyl 2-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl]hydrazinecarboxylate

HRID 1867561Notes

Reaction equation

HRID 1867561 reaction equation
[NH:1]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[NH2:2].C(N(CC)CC)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[Cl:36])[N:27]=[C:26]([C:37](Cl)=[O:38])[C:25]=2[CH3:40])=[CH:20][CH:19]=1>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[N:28]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[Cl:36])[N:27]=[C:26]([C:37]([NH:2][NH:1][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:38])[C:25]=2[CH3:40])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 152841395-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carbonyl chloride

Product 1

HCID 86618350tert-Butyl 2-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl]hydrazinecarboxylateYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1.82 g of tert-butyl hydrazinecarboxylate and 2.4 ml of triethylamine in 50 ml of DCM is cooled to 0° C., a solution of 5.24 g of the compound obtained in stage A in 50 ml of DCM is added and the mixture is left stirring while allowing the temperature to rise to AT. The reaction mixture is washed with water, with a buffer solution at pH=2 and with a saturated NaHCO3 solution, the organic phase is dried over MgSO4 and the solvent is evaporated under vacuum. The residue is taken up in isopropyl ether, pentane is added and the precipitate formed is filtered off. 6.2 g of the expected compound are obtained.

Workup

  1. waitthe mixture is left
  2. washThe reaction mixture is washed with water, with a buffer solution at pH=2 and with a saturated NaHCO3 solution
  3. dry with materialthe organic phase is dried over MgSO4
  4. customthe solvent is evaporated under vacuum
  5. additionpentane is added
  6. customthe precipitate formed
  7. filtrationis filtered off

Sources & evidence

ORD record
ord-9f968290a2174829ac2a4e5b603a43a6
Source dataset
uspto-grants-2009_12
Patent number
US07632852B2

Reaction notes

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