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

HRID 1688112Notes

Reaction equation

HRID 1688112 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>ClCCl>[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 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

At −75° C., chloroacetyl chloride (11.3 g, 8.1 mL, 0.1 mol) was added slowly to a suspension of methyl-phenethyl-amine (13.5 g, 0.1 mol), triethylamine (15 mL) in dichloromethane (50 mL). The suspension was warmed to 25° C. over the course of 3 hours and the salt was removed by filtration. The organic phase was washed with HCl solution (1 N, 200 mL), dried with sodium sulfate. The solvent was evaporated in vacuo to give 2-chloro-N-methyl-N-phenethyl-acetamide (20 g, 95%): 1H NMR (300 MHz, CDCl3) δ 7.2 (m, 5H), 4.03 (s, 3H), 3.6 (m, 2H), 2.99 (s, 2H), 2.8 (m, 2H).

Workup

  1. customthe salt was removed by filtration
  2. washThe organic phase was washed with HCl solution (1 N, 200 mL)
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b2c84e1e83e0433fa4d32e4390ae6774
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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