Hydrochloric Acid → 2-(2-Trifluoromethyl-thiazol-4-yl)morpholin-5-one

HRID 1451389Notes

Reaction equation

HRID 1451389 reaction equation
[H-].[Na+].[OH:3][CH:4]([C:7]1[N:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[S:10][CH:11]=1)[CH2:5][NH2:6].Cl[CH2:17][C:18](OCC)=[O:19].Cl>C1(C)C=CC=CC=1.O.C(O)C>[F:13][C:12]([F:15])([F:14])[C:9]1[S:10][CH:11]=[C:7]([CH:4]2[O:3][CH2:17][C:18](=[O:19])[NH:6][CH2:5]2)[N:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 140762394-Thiazolemethanol, alpha-(aminomethyl)-2-(trifluoromethyl)-

Product 1

HCID 140762422-(2-Trifluoromethyl-thiazol-4-yl)morpholin-5-one

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

0.3 g (0.0064 mol) of a dispersion of sodium hydride (50-55% in oil) is added in small portions to a stirred solution of 1 g (0.0047 mol) of 2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine in 15 ml of toluene at 30° C. After 1 hour a solution of 0.55 g (0.0045 mol) of ethyl chloroacetate in 2 ml of toluene is added dropwise. After 2 hours first 1 ml of ethanol and then 4 ml of water are added dropwise. The mixture is then acidified with hydrochloric acid and extracted several times with methylene chloride, and the extract is dried over sodium sulphate. The resulting product is purified on a silica gel column using ethyl acetate/methanol=1/1 as eluant and, after evaporation to dryness, digested with a little ether.

Workup

  1. extractionextracted several times with methylene chloride
  2. dry with materialthe extract is dried over sodium sulphate
  3. customThe resulting product is purified on a silica gel column
  4. customafter evaporation to dryness

Sources & evidence

ORD record
ord-1b9a54405bc94b2ab0b30cca45ddd849
Source dataset
uspto-grants-1997_02
Patent number
US05604225

Reaction notes

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