Benzoyl chloride → N-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}benzamide

HRID 1532370Notes

Reaction equation

HRID 1532370 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH2:20])=[CH:15][C:14]([N+:21]([O-:23])=[O:22])=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(N(CC)CC)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:15][C:14]([N+:21]([O-:23])=[O:22])=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 212499152-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethylamine

Product 1

HCID 21249902N-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}benzamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethylamine (3.0 g in 80 mL dry methylene chloride) at 0° C. was added 4.0 mL triethylamine followed by 1.4 mL benzoyl chloride and the mixture stirred at low temperature. After 20 minutes, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic portion was washed with water and concentrated in vacuo to give the crude title compound (1.43 g).

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic portion was washed with water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26864f2ae19b4ba1a52db124ed23e6b0
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

Loading…