Water → HCID 458932, compound

HRID 1393827Notes

Reaction equation

HRID 1393827 reaction equation
[Cl-].[NH4+].O.[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:9][CH:8]=1)([O-])=O>O.C(O)C.[Zn]>[NH2:4][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][NH:16][S:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 459019HCID 459019, compound

Product 1

HCID 458932HCID 458932, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of zinc powder (2 g) and ammonium chloride (0.2 g) in 22 ml of a water/ethanol mixture (1/1) was refluxed in a boiling-water bath. The derivative N-{2-[(4nitrophenyl)amino]ethyl}benzenesulfonamide (2) (3 g, 9 mmol) was added in portions and heating was continued until the reaction medium decolorized. The mixture was filtered while hot and the zinc was rinsed with ethanol/water solution (50/50). The filtrate crystallized rapidly. After cooling to 0° C., the solid was filtered off and then washed with water. After drying, 2.27 g of crude product with a melting point of 144° C. were obtained. 0.77 g of this crude product was recrystallized from 20 mL of water/ethanol (1/1), and the crystals obtained were dried over P2O5 and microanalysed.

Workup

  1. temperatureheating
  2. filtrationThe mixture was filtered while hot and the zinc
  3. washwas rinsed with ethanol/water solution (50/50)
  4. customThe filtrate crystallized rapidly
  5. filtrationthe solid was filtered off
  6. washwashed with water
  7. customAfter drying

Sources & evidence

ORD record
ord-913d8433d0c04c6db0e727bf7c61052d
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

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