Undec-4-ene → N-(n-pentanesulfonyl)-3-(acetylamino)-4-nitrobenzamide

HRID 1066337Notes

Reaction equation

HRID 1066337 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:8]([OH:10])=O)(=[O:3])[CH3:2].[CH2:17]([S:22]([NH2:25])(=[O:24])=[O:23])[CH2:18][CH2:19][CH2:20][CH3:21].CCCCCCC=CCCC>CN(C)C=O>[CH2:17]([S:22]([NH:25][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=1)(=[O:24])=[O:23])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 136496Undec-4-eneHCID 39330783-Acetamido-4-nitrobenzoic acidHCID 109206961-Pentanesulfonamide

Product 1

HCID 21198585N-(n-pentanesulfonyl)-3-(acetylamino)-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N′-carbonyldiimidazole (65.09 g) was added all at once to a solution (200 ml) of N,N-dimethylformamide containing 3-acetylamino-4-nitrobenzoic acid (60.22 g), and the reaction mixture was stirred at room temperature for 1 hour. 1-pentanesulfonamide (60.72 g) and 1,8-diazabicycle[5.4.0]undec-7-ene (61.12 g) were added thereto, and the mixture was stirred at 100° C. for 16 hours. The solvent was evaporated at 90° C. under reduced pressure using a vacuum pump. Chloroform and water were added to the resulting residue, and the pH of the aqueous layer was adjusted to 4 with diluted hydrochloric acid with stirring. The organic layer was separated, dried over sodium sulfate, and then concentrated to yield partially purified N-(n-pentanesulfonyl)-3-(acetylamino)-4-nitrobenzamide. The product was used immediately in the next reaction step.

Workup

  1. stirringthe mixture was stirred at 100° C. for 16 hours
  2. customThe solvent was evaporated at 90° C. under reduced pressure
  3. additionChloroform and water were added to the resulting residue
  4. stirringwith stirring
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a4315643472b47bb91338c44c329d259
Source dataset
uspto-grants-2001_06
Patent number
US06242474B1

Reaction notes

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