Thionyl Chloride → 4-(Chloromethyl)-2-(4-chloro-3-methylphenyl)-1,3-oxazole

HRID 508159Notes

Reaction equation

HRID 508159 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13]O)[N:12]=2)=[CH:4][C:3]=1[CH3:15].S(Cl)([Cl:18])=O>ClCCl>[Cl:18][CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:15])[CH:4]=2)[O:9][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58284347[2-(4-Chloro-3-methylphenyl)-1,3-oxazol-4-yl]methanol

Product 1

HCID 445419714-(Chloromethyl)-2-(4-chloro-3-methylphenyl)-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

136 mg (0.61 mmol) of the compound from Example 27A are suspended in 2 ml of dichloromethane. The suspension is cooled to 0° C., and 49 μl (0.67 mmol) of thionyl chloride are added slowly. The reaction solution is stirred at RT overnight. The solvent is then removed on a rotary evaporator. The residue is used without further purification in the subsequent reactions.

Workup

  1. customThe solvent is then removed on a rotary evaporator
  2. customThe residue is used without further purification in the subsequent reactions

Sources & evidence

ORD record
ord-11fa7d888c304aceb6bce33ccfc5a02c
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

Loading…