Chloroacetyl chloride → HCID 12032304, compound

HRID 929916Notes

Reaction equation

HRID 929916 reaction equation
[NH2:1][C@@H:2]([CH3:5])[CH2:3][OH:4].[Cl:6][CH2:7][C:8](Cl)=[O:9]>O.ClCCl.[OH-].[Na+]>[Cl:6][CH2:7][C:8]([NH:1][C@@H:2]([CH3:5])[CH2:3][OH:4])=[O:9]

Participants

6

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 80307L-Alaninol

Product 1

HCID 12032304HCID 12032304, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of (S)-2-aminopropan-1-ol (10 g, 0.13 mol) in water at 0° C. was added simultaneously a solution of chloroacetyl chloride (18 g, 0.16 mol) in dichloromethane (50 mL) and 1.6M aqueous sodium hydroxide (100 mL) dropwise over 1 h. The dichloromethane was removed under reduced pressure then the aqueous layer was extracted with ethyl acetate. The separated organic layer was dried (Na2SO4) and concentrated to afford (S)-2-chloro-N-(1-hydroxypropan-2-yl)acetamide (16.2 g, 83%) as a colourless oil which was used in the next step without further purification.

Workup

  1. customThe dichloromethane was removed under reduced pressure
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe separated organic layer was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0dc6e9e7b288400aaa0aebbeada202a2
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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