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Chloroacetyl chloride → 2-Chloro-N-(2,2-dimethoxyethyl)acetamide

HRID 262932
Notes
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Reaction equation

HRID 262932 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[OH-].[Na+].[Cl:10][CH2:11][C:12](Cl)=[O:13]>ClCCl>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:12](=[O:13])[CH2:11][Cl:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 193700222-Chloro-N-(2,2-dimethoxyethyl)acetamideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 105.1 grams (g) (1.0 moles) of aminoacetaldehyde dimethyl acetal, 80 g (1.0 moles) of a 50% aqueous solution of sodium hydroxide, and 200 ml dichloromethane are placed in a 1 liter flask fitted with a stirrer and thermometer. To this is added 113.0 g (1.0 moles) of chloroacetyl chloride dropwise with rapid stirring at 0°-10° C. After the addition is complete, the reaction is allowed to rise to room temperature and is stirred for 1 hour. Next the mixture is washed with 100 ml water, 100 ml sodium carbonate solution and 100 ml water, followed by drying and evaporation to give 113.8 g (63% yield) of the title compound, m.p. 33°-36° C.

Workup

  1. customare placed in a 1 liter flask
  2. customfitted with a stirrer
  3. additionAfter the addition
  4. customto rise to room temperature
  5. stirringis stirred for 1 hour
  6. washNext the mixture is washed with 100 ml water, 100 ml sodium carbonate solution and 100 ml water
  7. customby drying
  8. customevaporation

Sources & evidence

ORD record
ord-2c346f88679d426a850eb7e800436b60
Source dataset
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04155745

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes