Water → N-(2-Fluoro-5-nitrophenyl)-2-methoxyacetamide

HRID 1357696Notes

Reaction equation

HRID 1357696 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[F:7][C:8]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:9]=1[NH2:10].C(N(CC)CC)C.O>C(Cl)Cl>[F:7][C:8]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:9]=1[NH:10][C:4](=[O:5])[CH2:3][O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 677852-Fluoro-5-nitroanilineHCID 96623Methoxyacetyl chloride

Product 1

HCID 2290733N-(2-Fluoro-5-nitrophenyl)-2-methoxyacetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methoxyacetyl chloride (5.85 ml) in methylene chloride (50 ml) was added dropwise to a solution of 2-fluoro-5-nitroaniline (5.06 g) and triethylamine (8.92 ml) in methylene chloride (150 ml) under an argon atmosphere. The resultant mixture was stirred at ambient temperature for 5 hours, then poured into water and extracted with methylene chloride. The organic phases were washed with brine, dried over magnesium sulphate, filtered and evaporated to dryness to yield N-(2-fluoro-5-nitrophenyl)-2-methoxyacetamide as a solid (7.7 g, 100%); NMR: 3.26 (s, 2H), 4.5 (s, 3H), 7.57 (t, 1H), 8.03 (m, 1H), 8.82 (m, 1H), 9.83 (s, 1H); m/s: M+H+ 229.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phases were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-410c0b20f9a243c7a5374a152b4ab5af
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

Loading…