Thionyl Chloride → 4-(Chloromethyl)-2-(propan-2-yl)-1,3-oxazole

HRID 2210954Notes

Reaction equation

HRID 2210954 reaction equation
[Cl:1][CH2:2][C:3]1(O)[CH2:7][O:6][C:5]([CH:8]([CH3:10])[CH3:9])=[N:4]1.O=S(Cl)Cl>ClCCCl>[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[O:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 107498144-Chloromethyl-4-hydroxy-2-isopropyoxazoline

Product 1

HCID 27632914-(Chloromethyl)-2-(propan-2-yl)-1,3-oxazoleYield 96%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 4-chloromethyl-4-hydroxy-2-isopropyloxazoline (4.88 g, 0.0275 mol) in 1,2-dichloroethane (20 mL) was added to a solution of SOCl2 (2.40 mL, 0.0329 mol)in 1,2-dichloroethane (80 mL) at 0° C. under argon, and the solution was heated to 70° C. After 15 min at 70° C., the reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. Drying the residue on high vacuum gave the desired compound as a brown semi-solid (4.20 g, 0.0263 mol, 96%):

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customthe solvent removed by rotary evaporation in vacuo
  3. customDrying the residue on high vacuum

Sources & evidence

ORD record
ord-e605d1d63e95428ba05f6a0e3fac9cf4
Source dataset
uspto-grants-1995_10
Patent number
US05461067

Reaction notes

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