Water → HCID 69203940, compound

HRID 1393832Notes

Reaction equation

HRID 1393832 reaction equation
[Cl-:1].[NH4+].O.[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][S:16]([NH:19][CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)(=[O:18])=[O:17])=[CH:9][CH:8]=1)([O-])=O>[Zn].C(O)C>[ClH:1].[ClH:1].[NH2:4][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][S:16]([NH:19][CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)(=[O:18])=[O:17])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 69205254HCID 69205254, compound

Product 1

HCID 69203940HCID 69203940, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A mixture of zinc powder (3.8 g), ammonium chloride (0.22 g), water (0.75 mL), and 96% ethanol (10 mL) was refluxed in a boiling water bath. The derivative 2-[(4-nitrophenyl)amino]-N-(tetrahydrofuran-2-ylmethyl)ethanesulfonamide (10) (2.52 g, 7.6 mmol) was added in portions and heating was continued until the reaction medium decolorized. The resulting mixture was filtered while boiling and the filtrate was recovered onto 12 mL of ethanol and 1.5 mL of concentrated hydrochloric acid. Acetone was added to precipitate the hydrochloride formed (1.8 g). The product was filtered off and recrystallized from 15 mL of ethanol to give 0.8 g of dihydrochlorided product with the following elemental analyses:

Workup

  1. temperaturewas refluxed in a boiling water bath
  2. temperatureheating
  3. filtrationThe resulting mixture was filtered
  4. customthe filtrate was recovered onto 12 mL of ethanol and 1.5 mL of concentrated hydrochloric acid
  5. additionAcetone was added
  6. customto precipitate the hydrochloride
  7. customformed (1.8 g)
  8. filtrationThe product was filtered off
  9. customrecrystallized from 15 mL of ethanol

Sources & evidence

ORD record
ord-38eb258731ee4b41aca21ddbf71953b8
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

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