Methoxyacetyl chloride → HCID 18412576, compound

HRID 50205Notes

Reaction equation

HRID 50205 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:14][O:15][CH2:16][C:17](Cl)=[O:18]>ClC1C=CC=CC=1>[F:13][C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[NH:1][C:17](=[O:18])[CH2:16][O:15][CH3:14]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 18412404Ethyl 3-amino-4-fluorobenzoate

Product 1

HCID 18412576HCID 18412576, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 2.8 g (15.3 mmol) of ethyl 3-amino-4-fluorobenzoate (cf L. S. Fosdick and A. F. Dodds in J. Amer. Chem. Soc. 65, 2305 (1943)) and 1.56 mL (1.85 g=17.0 mmol) of methoxyacetylchloride in 50 mL chlorobenzene was stirred for 1 hour at 50° C. and then refluxed for 15 minutes. Then the solvent was distilled off in vacuo and the crude product obtained was purified by flash chromatography (silica gel; dichloromethane/ethanol=100:1). The desired compound, initially oily, solidified within a few days. Yield: 3.8 g (98% of theory); Rf value: 0.38 (silica gel; dichloromethane/ethanol=19:1).

Workup

  1. temperaturerefluxed for 15 minutes
  2. distillationThen the solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-a75db7d0746346e18fd4003918777c46
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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