Diethyl Carbonate → 5-(Hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-one

HRID 1462871Notes

Reaction equation

HRID 1462871 reaction equation
[C:1]1([NH:7][CH2:8][CH:9]([OH:12])[CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14]CCOC.C(=O)(OCC)OCC.C[O-].[Na+]>O>[OH:11][CH2:10][CH:9]1[O:12][C:13](=[O:14])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8]1

Participants

6

Reactant 4

HCID 7766Diethyl CarbonateHCID 80711,2-DimethoxyethaneHCID 915513-(N-Phenylamino)-1,2-propanediolHCID 10942334Sodium Methoxide

Product 1

HCID 2071325-(Hydroxymethyl)-3-phenyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 83.6 g (0.5 mole) of 3-phenylamino-1,2-propanediol, 250 ml of 1,2-dimethoxyethane and 61 ml of diethyl carbonate was refluxed in a nitrogen atmosphere. Solid sodium methoxide (about 0.15 g) was added and refluxing continued for approximately 21/2 hours. The mixture was cooled, stirred with water and filtered to yield 41.1 g of 5-(hydroxymethyl)-3-phenyl-2-oxazolidinone, m.p. 122°-124° C. The 41.1 g was recrystallized from 100 ml of absolute ethanol to give 38.0 g, m.p. 125.5°-126° C. A further crop of 25.3 g (m.p. 124.5°-125° C.) was obtained from the water filtrate by concentrating and recrystallizing from ethanol.

Workup

  1. temperaturewas refluxed in a nitrogen atmosphere
  2. temperaturerefluxing
  3. custom2 hours
  4. temperatureThe mixture was cooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-11c3b13858854fb8b368626e13fbf7a0
Source dataset
uspto-grants-1984_07
Patent number
US04461773

Reaction notes

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