Chloroacetyl chloride → 2-chloro-N-(3,4,5-trimethoxyphenyl)acetamide

HRID 490163Notes

Reaction equation

HRID 490163 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[Cl:14][CH2:15][C:16](Cl)=[O:17]>C1(C)C=CC=CC=1>[Cl:14][CH2:15][C:16]([NH:6][C:5]1[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:17]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 322853,4,5-Trimethoxyaniline

Product 1

HCID 21133062-chloro-N-(3,4,5-trimethoxyphenyl)acetamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,4,5-Trimethoxyaniline (Aldrich, 4.06 g, 22.2 mmol) and chloroacetyl chloride (2.60 mL, 32.7 mmol) in toluene (50 mL) were heated at 100° C. for 24 hours. The mixture was allowed to cool to room temperature and the volatiles were removed under reduced pressure. The residue was taken up in toluene and concentrated (3×) to remove traces of starting acid chloride and placed under high vacuum to provide 5.26 g (91%) of the title compound as a light brown solid. 1H NMR (500 MHz, DMSO-d6) δ 3.62 (s, 3H), 3.74 (s, 6H), 4.21 (s, 2H), 6.96 (s, 2H), 10.19 (br s, 1H); MS (DCI/NH3) m/e 260 (M+H)+.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. concentrationconcentrated (3×)
  3. customto remove traces of starting acid chloride

Sources & evidence

ORD record
ord-22dc8086dd9645c48bbeb1910457bc90
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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