Dimethylformamide → 4-(2-Cyanoethyl)-5-methyl-2-phenyloxazole

HRID 1294183Notes

Reaction equation

HRID 1294183 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([NH2:17])=O.CN(C)C=O.P(Cl)(Cl)(Cl)=O>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]#[N:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178613843-(5-Methyl-2-phenyl-4-oxazolyl)propanamide

Product 1

HCID 120932634-(2-Cyanoethyl)-5-methyl-2-phenyloxazoleYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-(5-methyl-2-phenyl-4-oxazolyl)propanamide (5.0 g) and N,N-dimethylformamide (100 ml) was added phosphoryl chloride (3.33 g) at room temperature and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give crystals (4.10 g, 89%) of 3-(5-methyl-2-phenyl-4-oxazolyl)propionitrile. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 63-64° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3b2e52956fe2447b9bbf38beea6e5d9f
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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