Hydrochloric Acid → 2-(4-Isopropylphenyl)-4,5-dimethyloxazole 3-oxide

HRID 748030Notes

Reaction equation

HRID 748030 reaction equation
[CH3:1]/[C:2](/[C:5]([CH3:7])=[O:6])=[N:3]\[OH:4].[CH3:8][CH:9]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)[CH3:10].Cl>C(O)(=O)C>[CH3:1][C:2]1[N+:3]([O-:4])=[C:15]([C:14]2[CH:17]=[CH:18][C:11]([CH:9]([CH3:10])[CH3:8])=[CH:12][CH:13]=2)[O:6][C:5]=1[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 326CuminaldehydeHCID 64096332,3-Butanedione monoxime

Product 1

HCID 597510222-(4-Isopropylphenyl)-4,5-dimethyloxazole 3-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

18.4 g of diacetyl monoxime and 29.6 g of 4(2-propyl)-benzaldehyde are added to 50 ml of glacial acetic acid, and HCl gas is introduced with ice-cooling for 30 minutes. The product is precipitated as the hydrochloride by addition of methyl tert-butyl ether and filtered off with suction, and the precipitate is washed with methyl tert-butyl ether. The precipitate is suspended in a mixture of dichloromethane and water, and a basic pH is established using ammonia. The mixture is extracted three times with, in each case, 500 ml of dichloromethane and ethyl acetate, the combined organic phases are dried over MgSO4 and the solvent is then removed under reduced pressure. This gives 38.2 g 4,5-dimethyl-2-(4-(2-propyl)-phenyl)-oxazole 3-oxide as a yellowish solid.

Workup

  1. additionis introduced with ice-
  2. temperaturecooling for 30 minutes
  3. customThe product is precipitated as the hydrochloride by addition of methyl tert-butyl ether
  4. filtrationfiltered off with suction
  5. washthe precipitate is washed with methyl tert-butyl ether
  6. additionThe precipitate is suspended in a mixture of dichloromethane and water
  7. extractionThe mixture is extracted three times with, in each case, 500 ml of dichloromethane and ethyl acetate
  8. dry with materialthe combined organic phases are dried over MgSO4
  9. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-6517fd32a288428ab9212a0b1eb482b2
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Reaction notes

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