Water → 4,4-dimethyl-2-(4-methylphenyl)-5H-1,3-oxazole

HRID 1881722Notes

Reaction equation

HRID 1881722 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=O)=[CH:10][CH:9]=1.O=S(Cl)Cl.O>C(Cl)Cl>[CH3:5][C:2]1([CH3:6])[CH2:3][O:4][C:7]([C:8]2[CH:16]=[CH:15][C:11]([CH3:12])=[CH:10][CH:9]=2)=[N:1]1

Participants

6

Reactant 4

HCID 962WaterHCID 118072-Amino-2-methyl-1-propanolHCID 134054-Methylbenzoyl Chloride2×HCID 24386Thionyl Chloride

Product 1

HCID 36949804,4-dimethyl-2-(4-methylphenyl)-5H-1,3-oxazoleYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-2-methyl-propanol (14.5 ml, 151 mmol) was stirred in 30 ml CH2Cl2 at 0° C. 4-Methylbenzoyl chloride (p-toluoyl chloride) (4c) (11.69 g, 75.6 mmol) was added dropwise. 4-Methylbenzoyl chloride may be prepared by conventional processes. The mixture was stirred for 4 hrs, at which time 11 ml of SOCl2 (151 mmol) was added slowly. The mixture was warmed to room temperature overnight. Water (30 ml) was added, the layers separated, and the organic layer washed with water (5×20 ml). The combined water layer was rinsed once with 15 ml CH2Cl2, and then basified with aqueous ammonia. The cloudy mixture was extracted with CH2Cl2 (3×30 ml), dried over MgSO4, filtered and the solvent evaporated to yield 10.7 g as a white crystalline solid (75% yield).

Workup

  1. additionwas added slowly
  2. customthe layers separated
  3. washthe organic layer washed with water (5×20 ml)
  4. washThe combined water layer was rinsed once with 15 ml CH2Cl2
  5. extractionThe cloudy mixture was extracted with CH2Cl2 (3×30 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-fcee25ba92a0477f93e1315d27526c0e
Source dataset
uspto-grants-2012_11
Patent number
US08318938B2

Reaction notes

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