Benzoyl chloride → N-(2',2'-dimethoxyethyl)-N-(2,6-dimethylphenyl)-benzamide

HRID 1578120Notes

Reaction equation

HRID 1578120 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][CH:12]([O:23][CH3:24])[CH2:13][NH:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22].C(N(CC)CC)C>C(OCC)C>[CH3:10][O:11][CH:12]([O:23][CH3:24])[CH2:13][N:14]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22])[C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 53799322N-(2,2-Dimethoxyethyl)-2,6-dimethylaniline

Product 1

HCID 20474701N-(2',2'-dimethoxyethyl)-N-(2,6-dimethylphenyl)-benzamideYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.81 g (0.02 mol) of benzoyl chloride were added in drops in 20 minutes and at a temperature of 0°-5° C. to a solution of N-(2',2'-dimethoxy-ethyl)-2,6-dimethyl aniline (4.45 g; 0.02 mol) in ethyl ether (20 ml) containing triethylamine (2.76 ml; 0.02 mol). The reaction mixture was stirred at room temperature for 15 minutes. The resulting salt was filtered and the solution was washed with 8 ml of an aqueous solution of hydrochloric acid at 5% and then with water up to neutral pH. The organic phase was anhydrified with anhydrous NaSO4 and the solvent was evaporated, so obtaining 5.2 g of a white solid which, recrystallized from petroleum ether (25 ml) provided 4.5 g of product (purity=91% by GLC) with a yield of 65.5% (white solid, melting point=58°-59° C.).

Workup

  1. filtrationThe resulting salt was filtered
  2. washthe solution was washed with 8 ml of an aqueous solution of hydrochloric acid at 5%
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3cecebf73a0346f897b9776f86f0146c
Source dataset
uspto-grants-1981_09
Patent number
US04291049

Reaction notes

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