Ammonium Chloride → HCID 86679431, compound

HRID 1776479Notes

Reaction equation

HRID 1776479 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=2[NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:3][CH2:2]1.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:12][C:10]1[CH:9]=[CH:8][C:7]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:11]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 14819589HCID 14819589, compound

Product 1

HCID 86679431HCID 86679431, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-(2-(cyclopropylmethoxy)-4-nitrophenyl)methanesulfonamide (0.830 g, 2.90 mmol), iron (0.971 g, 17.39 mmol), and NH4Cl (0.099 g, 1.848 mmol) in EtOH (15 ml) and water (6 ml) was heated to reflux for 30 minutes. The hot reaction mixture was filtered and the filtrate was evaporated. The residue was portioned between EtOAc and water; the organic phase was washed with brine and dried over Na2SO4. The solvent was removed affording N-(4-amino-2-(cyclopropylmethoxy)phenyl)-methanesulfonamide (0.679 g, 2.65 mmol, 91% yield, MS/ESI+ 256.9 [MH]+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. filtrationThe hot reaction mixture was filtered
  4. customthe filtrate was evaporated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-3ae80c44bc204d5887c0a5fde58c0ec7
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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