HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Benzoyl chloride → Benzamide, N-(1,1-dimethylethyl)-N-methyl-

HRID 466198
Notes
Print preview

Reaction equation

HRID 466198 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 527034Benzamide, N-(1,1-dimethylethyl)-N-methyl-Yield 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-380726716a064eefb7e30099ab4afbc2
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05155117

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes