Benzylamine → N-benzyl-3-nitrobenzamide

HRID 1418860Notes

Reaction equation

HRID 1418860 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C>[C:14]1([CH2:13][NH:20][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 347075N-benzyl-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A sample of m-nitrobenzoyl chloride, 7.4 g in 300 ml of ethyl acetate was treated with 11 ml of benzyl amine. After 30 minutes, the mix was washed with 100 ml of water. The ethyl acetate layer was concentrated hot to 100 ml and diluted with heptane until solids formed, and then the mix was stirred overnight and allowed to cool to 20° C. The solids were then collected to give N-phenylmethyl-3-nitrobenzamide, m.s. (M+H)+ =257

Workup

  1. washthe mix was washed with 100 ml of water
  2. concentrationThe ethyl acetate layer was concentrated hot to 100 ml
  3. additiondiluted with heptane until solids
  4. customformed
  5. customThe solids were then collected

Sources & evidence

ORD record
ord-d89849c56631463b90662e62dad5ccf4
Source dataset
uspto-grants-1999_03
Patent number
US05885985

Reaction notes

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