4-Chlorophenyl Isocyanate → 1H-Pyrazole-4-carboxylic acid, 3-(4-chlorophenyl)-1-(((4-chlorophenyl)amino)carbonyl)-4,5-dihydro-4-methyl-, methyl ester

HRID 1607223Notes

Reaction equation

HRID 1607223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:14]([O:16][CH3:17])=[O:15])([CH3:13])[CH2:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1>CCOCC>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([N:10]2[CH2:11][C:12]([C:14]([O:16][CH3:17])=[O:15])([CH3:13])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:9]2)=[O:27])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 198521233-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 1758551H-Pyrazole-4-carboxylic acid, 3-(4-chlorophenyl)-1-(((4-chlorophenyl)amino)carbonyl)-4,5-dihydro-4-methyl-, methyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An ether solution of 3-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole (Example O) (approximately 1.8 mole) is treated with 286 g (1.86 mole) of 4-chlorophenyl isocyanate at a rate sufficient to maintain a mild reflux. After stirring for 30 minutes solvent is removed to 2/3 of the volume to afford a semisolid. After cooling in an ice bath solid product is filtered and washed with cold hexane and dried yielding 702 g (95%) of N,3-bis-(4-chlorophenyl)-4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide. NMR data was consistent with the structure.

Workup

  1. temperatureto maintain a mild reflux
  2. customis removed to 2/3 of the volume
  3. customto afford a semisolid
  4. temperatureAfter cooling in an ice bath solid product
  5. filtrationis filtered
  6. washwashed with cold hexane
  7. customdried

Sources & evidence

ORD record
ord-1d5b1dc7db1e471fa7f2bef9d4ebbcad
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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