4-(Trifluoromethyl)phenyl isocyanate → HCID 18980935, compound

HRID 482620Notes

Reaction equation

HRID 482620 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([N:13]([CH2:22][CH2:23][CH3:24])[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])[CH2:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>CCOCC>[F:25][C:26]([F:36])([F:37])[C:27]1[CH:28]=[CH:29][C:30]([NH:33][C:34]([N:10]2[CH2:11][CH:12]([N:13]([CH2:22][CH2:23][CH3:24])[C:14]([O:16][CH2:17][C:18]([Cl:19])([Cl:21])[Cl:20])=[O:15])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:9]2)=[O:35])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 18980964HCID 18980964, compound

Product 1

HCID 18980935HCID 18980935, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

To half of the ether solution of 3-(4-chlorophenyl)-4-(N-propyl-N-(2,2,2-trichloroethoxycarbonyl)-amino)-4,5-dihydro-1H-pyrazole (Example 349c) (≤149 mmole) was added 18.7 g (100 mmole) of 4-trifluoromethylphenyl isocyanate. After stirring for 30 minutes, the mixture was concentrated in vacuo and dissolved in 200 ml of 50/50 diethyl ether/hexanes and cooled to -20° C. Crystals of the desired compound formed and were filtered yielding 30 g of the desired compound, mp 172°-173° C.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutiondissolved in 200 ml of 50/50 diethyl ether/hexanes

Sources & evidence

ORD record
ord-a6c8cd737eed452590327b27b3406208
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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