Acetyl chloride → Acetamide, N-(3-chloro-4-methoxyphenyl)-

HRID 2064681Notes

Reaction equation

HRID 2064681 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:18](=[O:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 214413-Chloro-4-methoxyaniline

Product 1

HCID 23474Acetamide, N-(3-chloro-4-methoxyphenyl)-Yield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-chloro-4-methoxyphenylamine (6.3 g) and triethylamine (4.04 g) in dichloromethane (100 mL) was chilled in an ice bath, acetyl chloride (3.45 g) was added dropwise and the mixture was stirred at ambient temperature overnight. The reaction mixture was extracted with water (2×30 mL) and brine (2×30 mL) and the organic layer was dried with magnesium sulfate. The drying agent was removed by filtration and the filtrate was evaporated to give N-(3-chloro-4-methoxyphenyl)acetamide (7.45 g) as a dark oil, which solidified on standing. MS: 200 (M+H)+.

Workup

  1. extractionThe reaction mixture was extracted with water (2×30 mL) and brine (2×30 mL)
  2. dry with materialthe organic layer was dried with magnesium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9000109d7fb94fbfbd070e561526d167
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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