2-(2-Chloroethoxy)acetyl chloride → Ethyl {4-[2-(2-chloroethoxy)acetylamino]phenyl}acetate

HRID 602345Notes

Reaction equation

HRID 602345 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6](Cl)=[O:7].Cl.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:16]=1)=[O:7]

Participants

4

Reactant 2

HCID 190484202-(2-Chloroethoxy)acetyl chlorideHCID 24192282Ethyl (4-aminophenyl)acetate--hydrogen chloride (1/1)

Product 1

HCID 58691225Ethyl {4-[2-(2-chloroethoxy)acetylamino]phenyl}acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

14.6 g (92.7 mmol) of (2-chloroethoxy)acetyl chloride are added to a suspension of 20.0 g (92.7 mmol) of ethyl 4-aminophenylacetate hydrochloride in 25 ml of toluene, and the mixture is heated at the boil for 24 hours. The reaction mixture is evaporated and dried, giving ethyl {4-[2-(2-chloroethoxy)acetylamino]phenyl}acetate as a yellowish solid; ESI 300.

Workup

  1. temperaturethe mixture is heated at the boil for 24 hours
  2. customThe reaction mixture is evaporated
  3. customdried

Sources & evidence

ORD record
ord-5e128d9d77c543eb915b125896f28f68
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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