Triethylamine → Methyl 3-(4-chlorophenyl)-4-methyl-1-{[4-(trifluoromethyl)phenyl]carbamoyl}-4,5-dihydro-1H-pyrazole-4-carboxylate

HRID 1607228Notes

Reaction equation

HRID 1607228 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.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1>C(Cl)Cl>[F:26][C:27]([F:37])([F:38])[C:28]1[CH:29]=[CH:30][C:31]([NH:34][C:35]([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:36])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 198521223-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride

Product 1

HCID 108039Methyl 3-(4-chlorophenyl)-4-methyl-1-{[4-(trifluoromethyl)phenyl]carbamoyl}-4,5-dihydro-1H-pyrazole-4-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole hydrochloride (Example P) (10 mmole), triethylamine (20 mmole), methylene chloride (30 ml) were added together and stirred for 10 minutes, whereon 10 mmole of 4-trifluoromethylphenyl isocyanate was added and after 30 minutes the resulting mixture was washed twice with water, dried with magnesium sulfate and concentrated giving a 95% yield of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide. NMR data was consistent with the structure.

Workup

  1. additionwas added and after 30 minutes the resulting mixture
  2. washwas washed twice with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e2c2c168c6e64ba5af9d5fef24427ded
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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