N-Methylbenzylamine → HCID 306531, compound

HRID 450054Notes

Reaction equation

HRID 450054 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[N+:17]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24])([O-:19])=[O:18]>C1COCC1.C(OCC)(=O)C>[CH2:3]([N:2]([CH3:1])[C:23](=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 306531HCID 306531, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methyl benzylamine (600 mg, 5 mmol) and triethylamine (1.5 ml, 10 mmol) in anhydrous THF (15 ml), was slowly added 3-nitro benzoyl chloride (1 g, 5.4 mmol) and stirred overnight at room temperature. The solvent was evaporated to give a residue which was dissolved in ethyl acetate and washed thoroughly with water. The organic layer was dried and evaporated to give N-benzyl-N-methyl-3-nitro-benzamide (350 mg, 27%) as solid.

Workup

  1. customThe solvent was evaporated
  2. customto give a residue which
  3. washwashed thoroughly with water
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-fd1973b7b8bf4d3db0b06898f1134250
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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