Chloroacetyl chloride → HCID 55298424, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- customAfter the removal of the solvents the residue
- additionwas diluted with 50 mL of 1:1 ethyl acetate/hexane
- stirringstirred for 30 min
- filtrationfiltered
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-453d25254100415e8c4f185997596c98
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622583B2
Reaction notes
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