Thionyl Chloride → 2-(Chloromethyl)-4-isopropylthiazole

HRID 1828426Notes

Reaction equation

HRID 1828426 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9]O)[S:7][CH:8]=1)([CH3:3])[CH3:2].S(Cl)([Cl:13])=O>ClCCl>[Cl:13][CH2:9][C:6]1[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10678505(4-Isopropylthiazol-2-yl)methanol

Product 1

HCID 220637012-(Chloromethyl)-4-isopropylthiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Isopropyl-1,3-thiazol-2-yl)methanol (10 g, 63.6011 mmol) dissolved in dichloromethane (60 ml) was added with thionyl chloride (7 ml, 95.40 mmol) under ice cooling, and then the reaction solution was returned to room temperature and stirred for 20 minutes. The reaction solution was concentrated under reduced pressure, and the residue was subjected to azeotropy with toluene and then diluted with diethyl ether, and further neutralized with saturated aqueous sodium hydrogencarbonate. The organic layer was washed with saturated brine, then dried over magnesium sulfate and concentrated under reduced pressure. The title compound was obtained as the residue without purification (11 g, 100%).

Workup

  1. customwas returned to room temperature
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additiondiluted with diethyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fcbe9d6305554594aba930bf6a6f069a
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

Loading…