Triphenylphosphine → HCID 19852596, compound

HRID 1607230Notes

Reaction equation

HRID 1607230 reaction equation
[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][C:16]([CH:19]=O)([CH3:18])[C:15]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:50]([F:55])([F:54])C([O-])=O.[Na+]>COCCOCCOC>[F:29][C:2]([F:1])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][C:16]([CH:19]=[C:50]([F:55])[F:54])([CH3:18])[C:15]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2734985Sodium chlorodifluoroacetateHCID 19852111HCID 19852111, compound

Product 1

HCID 19852596HCID 19852596, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

To 2.0 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-formyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide (5 mmole), was added 4 g of triphenylphosphine (15 mmole), 3 g of sodium chlorodifluoroacetate (20 mmole) and 15 ml of diglyme. The mixture was heated slowly to reflux over 1 hour. Gas evolved. After refluxing for 20 minutes the mixture was colled, partitioned between ether and water, dried, rotovaped and chromatographed (ether/hexane) to yield 0.5 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-(2,2-difluorovinyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide mp 142°-8° C. NMR data was consistent with the structure.

Workup

  1. temperatureThe mixture was heated slowly
  2. temperatureto reflux over 1 hour
  3. temperatureAfter refluxing for 20 minutes the mixture
  4. custompartitioned between ether and water
  5. customdried
  6. customchromatographed (ether/hexane)

Sources & evidence

ORD record
ord-89195e4201cd4eb38ed1c392a538a8a0
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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