Triethylamine → N-(3,5-dimethylisoxazol-4-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 1607231

Reaction equation

HRID 1607231 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:15]([O:17][CH3:18])=[O:16])([CH3:14])[CH2:12][NH:11][N:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:26][C:27]1[C:31]([N:32]=[C:33]=[O:34])=[C:30]([CH3:35])[O:29][N:28]=1>C(Cl)Cl>[CH3:26][C:27]1[C:31]([NH:32][C:33]([N:11]2[CH2:12][C:13]([C:15]([O:17][CH3:18])=[O:16])([CH3:14])[C:9]([C:6]3[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=3)=[N:10]2)=[O:34])=[C:30]([CH3:35])[O:29][N:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27362663,5-Dimethylisoxazole-4-isocyanateHCID 198521223-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride

Product 1

HCID 19852785N-(3,5-dimethylisoxazol-4-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride (10 mmole), triethylamine (20 mmole), methylene chloride (30 ml and 3,5-dimethylisoxazole-4-yl isocyanate (Maybridge Chemical Co. Ltd.) (10 mmole) were reacted by stirring at room temperature for 30 minutes. The reaction mixture was then washed twice with water, dried with magnesium sulfate concentrated giving a 95% yield of N-(3,5-dimethylisoxazol-4-yl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide mp 214°-216° C. NMR data was consistent with the structure.

Workup

  1. washThe reaction mixture was then washed twice with water
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-163a787293e64610890665b1deaaa9f7
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Linked notes

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