Sodium Methoxide → 5-(Hydroxymethyl)-3-[3-(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one

HRID 2082909Notes

Reaction equation

HRID 2082909 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([NH:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])[CH:6]=[CH:7][CH:8]=1.[C:17](=O)([O-])[O:18]CC.C[O-].[Na+]>CO>[OH:13][CH2:12][CH:11]1[O:14][C:17](=[O:18])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:15])([F:16])[F:1])[CH:4]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 21226545CID 21226545HCID 21328523HCID 21328523, compound

Product 1

HCID 2071305-(Hydroxymethyl)-3-[3-(trifluoromethyl)phenyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

59 G. OF 1-(M-TRIFLUOROMETHYL PHENYLAMINO)-2,3-PROPANEDIOL AND 118 G. OF ETHYL CARBONATE ARE INTRODUCED INTO A DISTILLATION APPARATUS. The mixture is progressively heated to about 110° C. when dissolution is obtained. Then, 12 ml. of a 5% solution of sodium methylate in methanol is added thereto. The distillation of the ethanol formed during the course of the reaction is then observed. Upon completion thereof any excess ethyl carbonate is removed under reduced pressure and the residue obtained is crystallized in isopropyl ether.

Workup

  1. dissolutionwhen dissolution
  2. customis obtained
  3. distillationThe distillation of the ethanol
  4. customformed during the course of the reaction
  5. customUpon completion thereof any excess ethyl carbonate is removed under reduced pressure
  6. customthe residue obtained
  7. customis crystallized in isopropyl ether

Sources & evidence

ORD record
ord-f5cbe5b0f66f4045bdfb55dfa50f699a
Source dataset
uspto-grants-1978_04
Patent number
USRE029607

Reaction notes

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