Chloroacetyl chloride → HCID 65312466, compound

HRID 1186384Notes

Reaction equation

HRID 1186384 reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].C(N(CC)CC)C.[Cl:14][CH2:15][C:16](Cl)=[O:17]>C(#N)C.CO>[Cl:14][CH2:15][C:16]([NH:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4])=[O:17]

Participants

5

Procedure

2-Amino-1,3-propanediol (5.24 g, 57.5 mmol) was dissolved in a mixed solvent (220 mL) of acetonitrile/methanol (6/1). To this, triethylamine (9.60 mL, 69.6 mmol) and chloroacetyl chloride (5.10 mL, 63.3 mmol) were successively added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=90/10) to give 2-chloro-N-(2-hydroxy-1-hydroxymethylethyl)acetamide (8.30 g, yield: 86%).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=90/10)

Sources & evidence

ORD record
ord-fe5c006f16b74acaa57ce3c23b4ef260
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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