Pyridine → 5-(3,4-Dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-ol

HRID 2052557Notes

Reaction equation

HRID 2052557 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[OH:4].[C:15](Cl)(Cl)=[O:16].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:3]2[O:4][C:15](=[O:16])[NH:1][CH2:2]2)[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 38639783,4-Dimethoxyphenylethanolamine

Product 1

HCID 30506615-(3,4-Dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-olYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

100 mmol of 2-amino-1-(3,4-dimethoxyphenyl)-ethanol is dissolved in 100 ml. of chloroform. After cooling to 0°, a solution of 100 mmol of phosgene in 100 ml. of chloroform is added dropwise so slowly that the internal temperature does not rise above 5°. After one hour of agitation at 5°-10°, 200 mmol of pyridine in 100 ml. of chloroform is added dropwise to the reaction mixture, and the latter is stirred for 3 hours. After washing the organic phase in semisaturated NaCl solution, the mixture is concentrated by evaporation and recrystallized from methanol, thus obtaining in a 75% yield 5-(3,4-dimethoxyphenyl)-2-oxazolidinone, m.p. 114°-117°.

Workup

  1. temperatureAfter cooling to 0°
  2. customdoes not rise above 5°
  3. washAfter washing the organic phase in semisaturated NaCl solution
  4. concentrationthe mixture is concentrated by evaporation
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9d00d2ccebb74492a46bfad4a3440339
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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