Triethylamine → N-[2-(Acetylamino)ethyl]-4-chlorobenzamide

HRID 2255112Notes

Reaction equation

HRID 2255112 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]([NH:14][CH2:15][CH2:16][NH2:17])(=[O:13])[CH3:12].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:11]([NH:14][CH2:15][CH2:16][NH:17][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 66082N-(2-aminoethyl)acetamide

Product 1

HCID 13576894N-[2-(Acetylamino)ethyl]-4-chlorobenzamideYield 78.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1.3 ml (0.01 mol) of 4-chlorobenzoyl chloride in 15 ml of chloroform is added dropwise at 0° to a solution of 1.02 g (0.01 mol) of acetylethylenediamine [J. Amer. Chem. Soc. 61, 822 (1939)] and 1.4 ml (0.01 mol) of triethylamine in 25 ml of chloroform. After 15 minutes, the resulting crystals are filtered off, washed with chloroform and dried. There are obtained 1.9 g of N-(2-acetylaminoethyl)-4-chlorobenzamide, m.p. 222°-224°.

Workup

  1. filtrationthe resulting crystals are filtered off
  2. washwashed with chloroform
  3. customdried

Sources & evidence

ORD record
ord-990ee1400a634730b18e021f82695c47
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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