Water → N-tert-Butyl-4-methylbenzamide

HRID 2092344Notes

Reaction equation

HRID 2092344 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12].O>C(Cl)Cl>[C:11]([NH:15][C:7](=[O:8])[C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 576940N-tert-Butyl-4-methylbenzamideYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of p-toluoyl chloride (34.2 ml, 259 mmol) in DCM (250 ml), charged to a 500 mL round bottom, t-butylamine (57.3 ml, 543 mmol) was added slowly at 0° C. The reaction mixture was stirred at 0° C. for 45 min. The reaction mixture was then partioned between additional DCM and water. The organic layer was then washed with water 2 and brine. The organic layer was then dried over magnesium sulfate and concentrated under vacuum to give a white solid N-tert-butyl-4-methylbenzamide (47.07 g, 95.1% yield). MS (M+H)+ 192.

Workup

  1. washThe organic layer was then washed with water 2 and brine
  2. dry with materialThe organic layer was then dried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-23827d8cbaa941588163605db538665f
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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