Phosgene → N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-methyl-4-isocyano-4,5-dihydro-1H-pyrazole-1-carboxamide

HRID 482602Notes

Reaction equation

HRID 482602 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][C:15]([CH3:20])([NH:17][CH:18]=O)[C:14]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.C(Cl)(Cl)=O>C(Cl)Cl>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][C:15]([CH3:20])([N+:17]#[C-:18])[C:14]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 18980948HCID 18980948, compound

Product 1

HCID 18980955N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-methyl-4-isocyano-4,5-dihydro-1H-pyrazole-1-carboxamideYield 17.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4.5 g (10 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-methyl-4-(N-formylamino)-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 64) and 3.4 ml (23 mmole) of triethylamine in 25 ml of methylene chloride at reflux was slowly added 5.5 ml of a 2.0M solution of phosgene in methylene chloride. After refluxing for 30 minutes the mixture was twice washed with water, dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and chromatographed on silica gel using diethyl ether and hexanes to yield 0.7 g of the title compound, a yellow solid, mp 171°-173° C.

Workup

  1. temperatureAfter refluxing for 30 minutes the mixture
  2. washwas twice washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-01854fcf28244784a0fc82d68541429c
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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