Sodium Chloride → Ethyl (1,3-thiazol-2-yl)acetate

HRID 881703Notes

Reaction equation

HRID 881703 reaction equation
[S:1]1[CH:5]=[CH:4][NH:3][C:2]1=[C:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl-].[Na+]>CS(C)=O.O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 10977652Diethyl 2-(thiazol-2(3H)-ylidene)malonate

Product 1

HCID 21835228Ethyl (1,3-thiazol-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A solution of the product of Example 44B (2.8 g, 11.5 mmoles), sodium chloride (1.3 g, 22.9 mmoles) and water (0.4 ml, 22.9 mmoles) in dimethyl sulfoxide (48.0 ml) was stirred at about 180° C. for about 30 min. The mixture was cooled, diluted with water (100.0 ml) and was extracted twice with (1:1) ethyl acetate/diethyl ether (80.0 ml each). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (2:1) as the mobile phase to provide the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. extractionwas extracted twice with (1:1) ethyl acetate/diethyl ether (80.0 ml each)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe crude product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-a6b2d65d7b084fb0bb4aef0b00e81d23
Source dataset
uspto-grants-2015_03
Patent number
US08993632B2

Reaction notes

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