Water → Ethyl [[2-(3-Chlorophenyl)-2-oxoethyl]amino](oxo)acetate

HRID 2301878Notes

Reaction equation

HRID 2301878 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)=[O:5].Cl[C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].O>C(Cl)Cl>[Cl:12][C:8]1[CH:7]=[C:6]([C:4](=[O:5])[CH2:3][NH:2][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 20884Ethoxalyl chlorideHCID 30262712-Amino-1-(3-chlorophenyl)ethanone hydrochloride

Product 1

HCID 85809577Ethyl [[2-(3-Chlorophenyl)-2-oxoethyl]amino](oxo)acetateYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-amino-1-(3-chlorophenyl)ethanone hydrochloride from Step 79a (2.83 g, 13.7 mmol, 1 eq), ethyl chlorooxoacetate (1.87 g, 13.7 mmol, 1 eq), and CH2Cl2 (40 mL) is cooled in an ice-H2O bath. The mixture is treated with a solution of TEA (4.0 mL, 29 mmol, 2.1 eq) in CH2Cl2 (20 mL), and the reaction is warmed to room temperature overnight. Water is added and the organic layer is separated, dried over MgSO4, filtered., and evaporated. The resulting solid is triturated with hexane/2-propanol and dried in vacuo to provide the title compound (2.70 g, 72%). MS (ESI) for C12H12ClNO4 m/z 270 (M+H)+.

Workup

  1. temperatureis cooled in an ice-H2O bath
  2. customthe organic layer is separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. custom, and evaporated
  6. customThe resulting solid is triturated with hexane/2-propanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d2b51a6f48944de1923abf378cf4311c
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

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