Water → HCID 11021483, compound

HRID 1266561Notes

Reaction equation

HRID 1266561 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-8d93214c67f348f58a5013c4d378afea
Source dataset
uspto-grants-2003_04
Patent number
US06548676B1

Reaction notes

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