Acetyl chloride → Acetamide, N-(4-fluoro-2-methoxyphenyl)-

HRID 130412Notes

Reaction equation

HRID 130412 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>ClCCl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:20])[CH3:19])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 135322284-Fluoro-2-methoxyaniline

Product 1

HCID 60740966Acetamide, N-(4-fluoro-2-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-fluoro-2-(methyloxy)aniline (Heterocycles 1992, 34, 2301-2311) (5.6 g, 40 mmol) and triethylamine (6.9 ml, 50 mmol) in dichloromethane (200 ml) at 0° C. was treated with acetyl chloride (2.85 ml, 40 mmol). After stirring at room temperature for 1 hour the solution was washed with 2N hydrochloric acid. The organic phase was separated, washed with water and brine then dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (1:5 to 1:2 ethyl acetate in dichloromethane) to afford the title compound. MS (ES+) m/e 184 [M+H]+.

Workup

  1. washwas washed with 2N hydrochloric acid
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (1:5 to 1:2 ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-87a41044c3874c8ba42d88c03d0b50d1
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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