3-(4-Chlorophenyl)-4,5-dihydro-1H-pyrazole → 1-[(3-Chloro-4-monochlorodifluoromethoxy-phenyl)-carbamoyl]-3-(4-chlorophenyl)-2-pyrazoline

HRID 1390971Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:12][CH:13]([F:15])[F:14])=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:27][CH2:26][NH:25][N:24]=2)=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:12][CH:13]([F:15])[F:14])=[C:4]([NH:9][C:10]([N:25]2[CH2:26][CH2:27][C:23]([C:20]3[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=3)=[N:24]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 80 °C

Procedure

12.7 g (0.05 mol) of 3-chloro-4-monochlorodifluoromethoxy-phenyl isocyanate in 20 ml of toluene were added, at 60° C., to a solution of 9 g (0.05 mol) of 3-(4-chlorophenyl)-2-pyrazoline in 60 ml of toluene. The batch was stirred for 2 hours at 80° C. On cooling to room temperature, the product precipitated and was filtered off. 8.5 g (39% of theory) of 1-[(3-chloro-4-monochlorodifluoromethoxy-phenyl)-carbamoyl]-3-(4-chlorophenyl)-2-pyrazoline with a melting point of 161° C. were obtained.

Workup

temperatureOn cooling to room temperature
customthe product precipitated
filtrationwas filtered off

Sources & evidence

ORD record: ord-6aeaf124f98345139a15bea2fee8b35e
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04140792

Reaction notes

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