Chloroacetyl chloride → 2-Chloro-N-methyl-N-(2-phenylethyl)acetamide

HRID 847143Notes

Reaction equation

HRID 847143 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>O1CCCC1>[Cl:1][CH2:2][C:3]([N:7]([CH3:6])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11503N-Methylbenzeneethanamine

Product 1

HCID 125579522-Chloro-N-methyl-N-(2-phenylethyl)acetamideYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of chloroacetylchloride (10.0 g, 88.7 mmol) in tetrahydrofuran (50 mL) was added to a solution of N-methylphenethylamine (10.0 g, 73.9 mmol) and triethylamine (11.2 g, 110.8 mmol) in tetrahydrofuran (200 mL) cooled by a water/ice bath. The reaction mixture was allowed to warm to ambient temperature. After stirring for 6 h, the reaction mixture was filtered and the filtrate was concentrated in vacuo to give SiO2, 1:1 ethyl acetate/hexane) to give 13.5 g (86.6%) of brown oil.

Workup

  1. temperaturecooled by a water/ice bath
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give SiO2, 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d76936358df6466996a8e398aa3a70fd
Source dataset
uspto-grants-1992_08
Patent number
US05140026

Reaction notes

Loading…