Tert-Butylamine → N-T-BUTYL-2-METHYLBENZAMIDE

HRID 2396090Notes

Reaction equation

HRID 2396090 reaction equation
[C:1]1([CH3:10])[C:2]([C:7](Cl)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C(N(CC)CC)C.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl.O>[C:18]([NH:22][C:7](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:10])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 702762-Methylbenzoyl chloride

Product 1

HCID 5071216N-T-BUTYL-2-METHYLBENZAMIDEYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cold (0° C.) solution of 139.2 g (0.9 mol) of o-toluoyl chloride in 1200 mL of methylene chloride at 25° C., under nitrogen, was slowly added 180.0 g (1.8 mol) of triethylamine followed by the dropwise addition of a solution containing 73.14 g (1.0 mol) of t-butylamine in 200 mL of methylene chloride. The resulting reaction mixture was warmed to room temperature and allowed to react for 2.5 hours.The reaction mixture was then diluted with 1800 mL of water. The resulting layers were separated, and the organic layer was washed sequentially with 2N sodium hydroxide, 1.0N hydrochloric acid and brine, dried over magnesium sulfate, filtered and then reduced to dryness under reduced pressure to provide 167.6 g of an off-white solid

Workup

  1. customat 25° C.
  2. additionfollowed by the dropwise addition of a solution
  3. customThe resulting reaction mixture
  4. customto react for 2.5 hours
  5. customThe resulting layers were separated
  6. washthe organic layer was washed sequentially with 2N sodium hydroxide, 1.0N hydrochloric acid and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-4cb293a190194bbaa07e976784a456d2
Source dataset
uspto-grants-1996_02
Patent number
US05491166

Reaction notes

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