Dimethylformamide → HCID 54157120, compound

HRID 1899065Notes

Reaction equation

HRID 1899065 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[CH:14][CH:13]=1>ClC(Cl)C>[Cl:3][C:18]([C:15]1[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=1)=[C:19]([C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 23372647HCID 23372647, compound

Product 1

HCID 54157120HCID 54157120, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

A mixture of phosphorus oxychloride (1.6 ml) and N,N-dimethylformamide (1.8 ml) in dichloroethane (6 ml) was stirred at ambient temperature for 1 hour. Dichloroethane (11 ml) and 4'-fluoro-2-(4-nitrophenyl)acetophenone (3 g) was added, and the mixture was refluxed overnight, washed with water twice, dried and evaporated. The oily residue (4 g) was purified by column chromatography on silica gel (80 g) eluting with toluene to give yellow crystals of 3-chloro-3-(4-fluorophenyl)-2-(4-nitrophenyl)propenal (2.9 g).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. washwashed with water twice
  3. customdried
  4. customevaporated
  5. customThe oily residue (4 g) was purified by column chromatography on silica gel (80 g)
  6. washeluting with toluene

Sources & evidence

ORD record
ord-bbac233a4d604856882eec1d4d6f9b20
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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