Water → HCID 19974322, compound

HRID 1451395Notes

Reaction equation

HRID 1451395 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[CH3:8][C:9]1[S:10][CH:11]=[C:12]([CH:14]=[O:15])[N:13]=1.O>CS(C)=O.CS(C)=O.O1CCCC1.O1CCCC1>[CH3:8][C:9]1[S:10][CH:11]=[C:12]([CH:14]2[O:15][CH2:2]2)[N:13]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 27631912-Methyl-1,3-thiazole-4-carbaldehyde

Product 1

HCID 19974322HCID 19974322, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolventHCID 21830753dimethylsulfoxide THFSolvent

Procedure

10.2 g (0.048 mol) of Trimethylsulphonium iodide are dissolved in 42 ml of dimethyl sulphoxide and added dropwise to a stirred solution, which is maintained at 0° C., of 1.14 g of sodium hydride in 50 ml of dimethyl sulphoxide/tetrahydrofuran (1:1). After 60 minutes, a solution of 6.1 g of 2-methyl-4-formyl-thiazole in 25 ml of tetrahydrofuran is added dropwise at 0° C., and the mixture is stirred at room temperature for 3 hours. It is then cooled to 0° C., 9.6 ml of water are added dropwise, and the mixture is extracted with ether. The ethereal phase is extracted by shaking 2× with water, dried and concentrated. The resulting oil is purified on a silica gel column using toluene/ethyl acetate (65:35) as eluant.

Workup

  1. additionadded dropwise to a stirred solution, which
  2. temperatureIt is then cooled to 0° C.
  3. extractionthe mixture is extracted with ether
  4. extractionThe ethereal phase is extracted
  5. stirringby shaking 2× with water
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting oil is purified on a silica gel column

Sources & evidence

ORD record
ord-1d60635976e14582903db82793b001ce
Source dataset
uspto-grants-1997_02
Patent number
US05604225

Reaction notes

Loading…