Chloroacetyl chloride → HCID 54028900, compound

HRID 1903005Notes

Reaction equation

HRID 1903005 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH2:7][CH2:8][NH:9][CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:6])[CH3:3].[Cl:21][CH2:22][C:23](Cl)=[O:24]>C1C=CC=CC=1>[CH2:2]([O:4][C:5]([CH2:7][CH2:8][N:9]([CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:23](=[O:24])[CH2:22][Cl:21])=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 86739296HCID 86739296, compound

Product 1

HCID 54028900HCID 54028900, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 14 g. (0.045 moles) of diethyl N-(2-ethoxycarbonylethyl)-amino-malonate hydrochloride prepared according to Example 1b) in 150 ml. of dry benzene 5.65 g. (4 ml., 0.05 moles) of chloroacetyl chloride are added with stirring. The mixture is boiled for 5 hours. The solution is evaporated in vacuo, the evaporation residue is triturated with 50 ml. of hexane, hexane is decanted and the same procedure is repeated two more times. The oily product is dried over sodium hydroxide in a vacuum desiccator. 13.6 g. (86%) of the named compound are obtained.

Workup

  1. additionTo a suspension of 14 g
  2. customThe solution is evaporated in vacuo
  3. customthe evaporation residue is triturated with 50 ml
  4. customof hexane, hexane is decanted
  5. dry with materialThe oily product is dried over sodium hydroxide in a vacuum desiccator

Sources & evidence

ORD record
ord-053d769cb633496f971dd2d4eee46a78
Source dataset
uspto-grants-1984_03
Patent number
US04435322

Reaction notes

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