Thionyl Chloride → N-[4-Chloro-2-methoxy-5-(1-methylethenyl)phenyl]acetamide

HRID 588868Notes

Reaction equation

HRID 588868 reaction equation
[Cl:1][C:2]1[C:7]([C:8](O)([CH3:10])[CH3:9])=[CH:6][C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([O:16][CH3:17])[CH:3]=1.O=S(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([CH3:10])=[CH2:9])=[CH:6][C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 117611023N-[4-Chloro-5-(1-hydroxy-1-methylethyl)-2-methoxyphenyl]acetamide

Product 1

HCID 90455956N-[4-Chloro-2-methoxy-5-(1-methylethenyl)phenyl]acetamideYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-chloro-5-(2-hydroxypropan-2-yl)-2-methoxyphenyl)acetamide (3.2 g, 12.4 mmol) in DCM (20 mL) at −5° C., SOCl2 (3.7 g, 37.25 mmol) was added dropwise. The mixture was warmed to RT, and then stirred at reflux for 2 h. The reaction mixture was concentrated and the residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=3:1) to afford the desired product (1.9 g, 64% yield).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=3:1)

Sources & evidence

ORD record
ord-b048965ea11e4db4a1b73f67d7975dd7
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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