Dimethylformamide → HCID 23024995, compound

HRID 349906Notes

Reaction equation

HRID 349906 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]2[CH:28]=[CH:27][C:12]([O:13][CH2:14][C:15]3[N:16]=[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[O:18][C:19]=3[CH3:20])=[CH:11][CH:10]=2)[N:3]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:36]=[O:37]>O>[CH3:1][C:2]1[C:6]([CH:36]=[O:37])=[C:5]([CH3:7])[N:4]([CH2:8][C:9]2[CH:28]=[CH:27][C:12]([O:13][CH2:14][C:15]3[N:16]=[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[O:18][C:19]=3[CH3:20])=[CH:11][CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 23024917HCID 23024917, compound

Product 1

HCID 23024995HCID 23024995, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[4-(3,5-dimethyl-1H-pyrazol-1-ylmethyl)phenoxymethyl]-5-methyl-2-phenyloxazole (1.62 g), phosphorus oxychloride (1.00 g), and N,N-dimethylformamide (20 ml) was stirred for 5 days at room temperature. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride solution, then dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and 3,5-dimethyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-carbaldehyde (950 mg, yield: 55%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0c8abdf8d583475ea2d0fc31ddb81cbe
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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