Dimethylformamide → HCID 178482591, compound

HRID 1288445Notes

Reaction equation

HRID 1288445 reaction equation
[I-:1].Cl[C:3]1[N:4]([CH3:15])[N+:5]([CH3:14])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[O-]C1C=CC=CC=1.[Na+].[CH3:24][N:25](C)[CH:26]=O>>[I-:1].[CH3:14][N+:5]1[N:4]([CH3:15])[C:3]([N:25]([CH3:26])[CH3:24])=[CH:7][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4445035Phenolate SodiumHCID 12665791HCID 12665791, compound

Product 1

HCID 178482591HCID 178482591, compound

Procedure

3-Chloro-1,2-dimethyl-5-phenylpyrazolium iodide (10.0 g, 0.03 mole) is treated with sodium phenoxide (5.64 g, 0.06 mole) in dimethylformamide (100 ml) and the mixture heated and stirred at 110° C to 120° C for 21 hours. The dimethylformamide is then removed in vacuo, the residual oil dissolved in aqueous sodium bicarbonate solution and is extracted with ether. The ether fraction yields some brown oil which is not further examined. Next the aqueous sodium bicarbonate solution is extracted with chloroform (2×150 ml). Evaporation of the chloroform solution yields a white solid which is dried by azeotropic distillation of toluene. Crystallization from a chloroform/ether mixture yields a white solid, m.p. 181.5° C to 182° C.

Workup

  1. temperaturethe mixture heated
  2. customThe dimethylformamide is then removed in vacuo
  3. dissolutionthe residual oil dissolved in aqueous sodium bicarbonate solution
  4. extractionis extracted with ether
  5. customThe ether fraction yields some brown oil which
  6. extractionNext the aqueous sodium bicarbonate solution is extracted with chloroform (2×150 ml)
  7. customEvaporation of the chloroform solution
  8. customyields a white solid which
  9. dry with materialis dried by azeotropic distillation of toluene
  10. customCrystallization from a chloroform/ether mixture
  11. customyields a white solid, m.p. 181.5° C to 182° C.

Sources & evidence

ORD record
ord-bc22923c24504e84a1f5e7ce80ea1381
Source dataset
uspto-grants-1976_10
Patent number
US03988348

Reaction notes

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