Ethanol → N-1-butanesulfonyl-3-amino-4-nitrobenzamide

HRID 1276940Notes

Reaction equation

HRID 1276940 reaction equation
[CH2:1]([S:5]([NH:8][C:9](=[O:23])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([NH:19]C(=O)C)[CH:11]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].C(O)C>O>[CH2:1]([S:5]([NH:8][C:9](=[O:23])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([NH2:19])[CH:11]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18315475N-1-butanesulfonyl-3-acetylamino-4-nitrobenzamide

Product 1

HCID 18315533N-1-butanesulfonyl-3-amino-4-nitrobenzamideYield 94.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 6.30 g of N-1-butanesulfonyl-3-acetylamino-4-nitrobenzamide, a 10% sodium hydroxide aqueous solution, 300 ml of ethanol and 200 ml of water was stirred at room temperature for 4 hours and then at 50° C. for 3 hours. The solvent was distilled off to approximately a half volume, and the residue was adjusted to a pH of 2 with 10% hydrochloric acid. The crystals precipitated were collected, and were dried under reduced pressure to give 5.22 g of N-1-butanesulfonyl-3-amino-4-nitrobenzamide.

Workup

  1. distillationThe solvent was distilled off to approximately a half volume
  2. customThe crystals precipitated
  3. customwere collected
  4. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-386332730d4e42a585ee8eaaf23ed35e
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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