Chloroacetyl chloride → HCID 65312466, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperaturecooling
- customAfter completion of the reaction
- customthe solvent was evaporated off under reduced pressure
- 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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