Benzoyl chloride → N-(tert-Butyl)-N-methylbenzamide

HRID 864454Notes

Reaction equation

HRID 864454 reaction equation
[CH3:1][NH:2][C:3]([CH3:6])([CH3:5])[CH3:4].C(N(CC)CC)C.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH3:1][N:2]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 84552N-Methyl-tert-butylamine

Product 1

HCID 527034N-(tert-Butyl)-N-methylbenzamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen, 96.7 g (1.1 mol) of N-methyl-N-tertbutylamine and 111 g (1.1 mol) of triethylamine was dissolved in 1050 mL of anhydrous tetrahydrofuran (THF). The solution was cooled to 0° C. and treated with 140.6 g (1.0 mol) of benzoyl chloride. The reaction was allowed to slowly warm to ambient temperature and stir overnight. Filtration and subsequent concentration in vacuo of the filtrate gave the crude product which was purified by sublimation (65°, 0.2 torr) to give 184 g (96%) of colorless N-methyl-N-tertbutybenzamide: mp 80.5°-82.0° C.; NMR (CDCl3) δ1.52 (s, 9H), 2.87 (s, 3H), 7.34-7.40 (m, 3H), 7.40-7.46 (m, 2H).

Workup

  1. temperatureto slowly warm to ambient temperature
  2. filtrationFiltration and subsequent concentration in vacuo of the filtrate
  3. customgave the crude product which
  4. customwas purified by sublimation (65°, 0.2 torr)

Sources & evidence

ORD record
ord-0de1aeae7a8c420982454e41611ec98b
Source dataset
uspto-grants-1996_10
Patent number
US05563139

Reaction notes

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