Triethylamine → HCID 22732315, compound

HRID 1357695Notes

Reaction equation

HRID 1357695 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[Cl:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([NH2:15])=[CH:10][C:9]=1[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(N(CC)CC)C>C(Cl)Cl>[Cl:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([NH:15][C:4](=[O:5])[CH2:3][O:2][CH3:1])=[CH:10][C:9]=1[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 22732259HCID 22732259, compound

Product 1

HCID 22732315HCID 22732315, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methoxyacetyl chloride (0.65 ml) was added dropwise to a solution of N-(2-chloro-4-fluoro-5-aminophenyl)phthalimide (1.39 g) and triethylamine (1.16 ml) in dry methylene chloride (45 ml) and the resulting mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with methylene chloride and washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulphate, filtered and evaporated to dryness to yield N-[2-chloro-4-fluoro-5-(2-methoxyacetamido)phenyl]phthalimide as a solid (1.72 g, 99%); NMR (CDCl3): 3.53 (s, 3H), 4.04 (s, 2H), 7.37 (d, 1H), 7.81 (m, 2H), 7.98 (m, 2H), 8.57 (d, 1H), 8.62 (broads s, 1H); m/s: [M−H]− 361, 363.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4acce5a4aaf54d6786cb8777940c1da0
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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