Acetic Anhydride → 3-Acetyl-5-(3,4-dimethoxyphenyl)-2-oxazolidinone

HRID 2052559Notes

Reaction equation

HRID 2052559 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[O:15][C:14](=[O:16])[NH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([N:13]1[CH2:12][CH:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[O:15][C:14]1=[O:16])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 30506615-(3,4-Dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-ol

Product 1

HCID 203762173-Acetyl-5-(3,4-dimethoxyphenyl)-2-oxazolidinoneYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.9 mmol of 5-(3,4-dimethoxyphenyl)-2-oxazolidinone is combined with 10 ml. of acetic anhydride and 5 ml. of pyridine and heated for 5 hours to 100°. After concentrating the reaction mixture, it is recrystallized from ethyl acetate, thus obtaining 3-acetyl-5-(3,4-dimethoxyphenyl)-2-oxazolidinone in a 73% yield, m.p. 175°-182°.

Workup

  1. concentrationAfter concentrating the reaction mixture, it
  2. customis recrystallized from ethyl acetate, thus obtaining 3-acetyl-5-(3,4-dimethoxyphenyl)-2-oxazolidinone in a 73% yield, m.p. 175°-182°

Sources & evidence

ORD record
ord-97ea86f2edc5482ea8e366bc7dbf8b27
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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