Chloroacetyl chloride → HCID 55298424, compound

HRID 419202Notes

Reaction equation

HRID 419202 reaction equation
[NH2:1][C@H:2]([CH3:5])[CH2:3][OH:4].[Cl:6][CH2:7][C:8](Cl)=[O:9]>C(Cl)Cl>[Cl:6][CH2:7][C:8]([NH:1][C@H:2]([CH3:5])[CH2:3][OH:4])=[O:9]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 80308(R)-(-)-2-Amino-1-propanol

Product 1

HCID 55298424HCID 55298424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of (R)-2-amino-propan-1-ol (2.0 g, 26.6 mmol) in 150 mL of DCM at −40° C. under nitrogen atmosphere was added dropwise chloroacetyl chloride (2.3 mL, 29.2 mmol) in 60 mL of DCM. The mixture was gradually warmed to 0° C. and was stirred for 2 hours. After the removal of the solvents the residue was diluted with 50 mL of 1:1 ethyl acetate/hexane, stirred for 30 min and filtered. The filtrate was concentrated to afford 2-chloro-N—((R)-2-hydroxy-1-methyl-ethyl)-acetamide as a liquid.

Workup

  1. customAfter the removal of the solvents the residue
  2. additionwas diluted with 50 mL of 1:1 ethyl acetate/hexane
  3. stirringstirred for 30 min
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fe60f5ae86514b30af39972671aadb52
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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