Ethanol → Benzamide,4-amino-n-(butylsulfonyl)-3-[[(2,4-dichlorophenyl)methyl]amino]-

HRID 1276942Notes

Reaction equation

HRID 1276942 reaction equation
[CH2:1]([S:5]([NH:8][C:9](=[O:29])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[CH:11]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(O)C.O1CCCC1>O>[CH2:1]([S:5]([NH:8][C:9](=[O:29])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[CH:11]=1)(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 18315434N-1-butanesulfonyl-3-(2,4-dichlorobenzylamino)-4-nitrobenzamide

Product 1

HCID 18315556Benzamide,4-amino-n-(butylsulfonyl)-3-[[(2,4-dichlorophenyl)methyl]amino]-Yield 46.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-1-butanesulfonyl-3-(2,4-dichlorobenzylamino)-4-nitrobenzamide (0.505 g) was added to a mixture of 1.32 g of sodium hydrosulfite, 1 ml of ethanol, 1 ml of tetrahydrofuran and 1 ml of water at room temperature. The mixture was heat-refluxed for 40 minutes. The solvent was distilled off under reduced pressure, and water was added to the residue. The solid material precipitated was collected, and was dried. Further, the resulting material was washed with a mixed solution of 10 ml of methanol and 3 ml of water, and was dried to give 0.220 g of N-1-butanesulfonyl-4-amino-3-(2,4-dichlorobenzylamino)benzamide.

Workup

  1. temperatureThe mixture was heat-refluxed for 40 minutes
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas added to the residue
  4. customThe solid material precipitated
  5. customwas collected
  6. customwas dried
  7. washFurther, the resulting material was washed with a mixed solution of 10 ml of methanol and 3 ml of water
  8. customwas dried

Sources & evidence

ORD record
ord-873f4b8db2ff475ba97ad43cc7344377
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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