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

HRID 1956524Notes

Reaction equation

HRID 1956524 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-ae76f9d530c84231a07fcc9548a4aace
Source dataset
uspto-grants-1998_07
Patent number
US05780437

Reaction notes

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