Chloroacetyl chloride → N-Benzyl-2-chloroacetamide

HRID 2065752Notes

Reaction equation

HRID 2065752 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19]>C1COCC1>[CH2:1]([NH:8][C:18](=[O:19])[CH2:17][Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 7504BenzylamineHCID 8471Triethylamine

Product 1

HCID 96233N-Benzyl-2-chloroacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzylamine (60.3 mL) and triethylamine (96.3 mL) in THF (800 mL) was added chloroacetyl chloride (45.8 mL) at 0° C. The reaction mixture was allowed to warm to room temperature over night. Additional chloroacetyl chloride (4.6 mL) was added and stirring was continued until no starting material could be detected. The reaction mixture was filtered, washed with ethyl acetate and concentrated. The crude product was crystallized from dichloromethane to yield N-benzyl-2-chloro-acetamide (71.6 g) as off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with ethyl acetate
  3. concentrationconcentrated
  4. customThe crude product was crystallized from dichloromethane

Sources & evidence

ORD record
ord-4887081dcc154031bff137c0a1a8006c
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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