Water → HCID 11021483, compound

HRID 2253298Notes

Reaction equation

HRID 2253298 reaction equation
[CH2:1]([S:8][C:9]1[S:10][C:11]([CH2:14]O)=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O.O>ClCCl>[CH2:1]([S:8][C:9]1[S:10][C:11]([CH2:14][Cl:18])=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 18551811HCID 18551811, compound

Product 1

HCID 11021483HCID 11021483, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1.18 g of 2-benzylsulfanyl-5-hydroxymethyl-thiazole dissolved in 5 ml of dichloromethane, 0.4 ml of thionyl chloride dissolved in 5 ml of dichloromethane are added dropwise at 0° C. to. The reaction mixture is then allowed to warm to room temperature and stirred for 0.5 hour. After the addition of 5 ml of water, the organic phase is washed twice with saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. After removal of the solvent in vacuo, chromatography on silica gel (ether:hexane; 1:4) yields 2-benzylsulfanyl-5-chloromethyl-thiazole having a melting point of 57-61° C.

Workup

  1. additionare added dropwise at 0° C. to
  2. washthe organic phase is washed twice with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of the solvent in vacuo, chromatography on silica gel (ether:hexane; 1:4)

Sources & evidence

ORD record
ord-30962eabca074bb2977c0f2810c1bb52
Source dataset
uspto-grants-2008_01
Patent number
US07323564B2

Reaction notes

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