Methylamine → N,3,4-trimethylbenzamide

HRID 1489647Notes

Reaction equation

HRID 1489647 reaction equation
[CH3:1][NH2:2].[CH3:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7](Cl)=[O:8]>O1CCCC1>[CH3:1][NH:2][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:12]([CH3:13])=[C:4]([CH3:3])[CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27585353,4-Dimethylbenzoyl chloride

Product 1

HCID 3341433N,3,4-trimethylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

108 ml of a 40 % strength aqueous solution of methylamine were dissolved in 300 ml of tetrahydrofuran. 53 g of 3,4-dimethylbenzoyl chloride were added dropwise to this solution with ice cooling. The reaction mixture was subsequently stirred at room temperature for 1 hour. Then the reaction mixture was concentrated to half its volume under reduced pressure, saturated sodium chloride solution was added, and the mixture was acidified with concentrated hydrochloric acid. The product which then precipitated was filtered out with suction and dried at 40° C. over potassium hydroxide in a drying cabinet. 47 g of N-methyl-3,4-dimethylbenzamide were obtained.

Workup

  1. concentrationThen the reaction mixture was concentrated to half its volume under reduced pressure, saturated sodium chloride solution
  2. additionwas added
  3. customThe product which then precipitated
  4. filtrationwas filtered out with suction
  5. dry with materialdried at 40° C. over potassium hydroxide in a drying cabinet

Sources & evidence

ORD record
ord-c8aa866a1d874e5e990234cd2daf5c34
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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