Triethylamine → HCID 86618351, compound

HRID 1867563Notes

Reaction equation

HRID 1867563 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.[Br: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[CH2:40][CH3:41])=[CH:20][CH:19]=1>C(Cl)Cl>[Br: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[CH2:40][CH3:41])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 112825495-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-1H-pyrazole-3-carbonyl chloride

Product 1

HCID 86618351HCID 86618351, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 3.2 g of tert-butyl hydrazinecarboxylate and 3.9 ml of triethylamine in 100 ml of DCM is cooled to 0° C., a solution of 10.5 g of the compound obtained in stage A in 100 ml of DCM is added dropwise and the mixture is left stirring while allowing the temperature to rise to AT. The reaction mixture is washed with water, with a pH=2 buffer solution and with a saturated NaHCO3 solution, the organic phase is dried over MgSO4 and the solvent is evaporated under vacuum. 12.7 g of the expected compound are obtained.

Workup

  1. waitthe mixture is left
  2. washThe reaction mixture is washed with water, with a pH=2 buffer solution and with a saturated NaHCO3 solution
  3. dry with materialthe organic phase is dried over MgSO4
  4. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-d53ea1ea28b44262a76b7e7bd0985f42
Source dataset
uspto-grants-2009_12
Patent number
US07632852B2

Reaction notes

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