Ammonium Chloride → HCID 22663759, compound

HRID 392395Notes

Reaction equation

HRID 392395 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=1)=[O:10].[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[NH2:17])=[O:10]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22663596HCID 22663596, compound

Product 1

HCID 22663759HCID 22663759, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Methoxy-2-(3-nitrophenylsulfinyl)benzene (217 mg, 0.78 mmol) was dissolved in ethyl alcohol (5.0 ml) and water (1.75 ml), to which was added iron powder (488 mg, 8.7 mmol) and ammonium chloride (77 mg, 1.4 mmol). This mixture was heated to reflux for four hours, cooled to room temperature and the supernatant decanted. The insoluble material was rinsed with methylene chloride, followed by aqueous 1M potassium carbonate. All decanted solutions were combined and the organic layer separated. The aqueous layer was extracted again with methylene chloride, and the combined organics washed once with brine. After drying over magnesium sulfate and concentration in vacuo, the title compound was obtained as a white solid (145 mg, 75%). 1H NMR(400 MHz): 3.89(3H,s), 6.69-6.74(1H,m), 6.86(1H,d,J=8.4), 7.03-7.09(2H,m), 7.10-7.20(2H,m), 7.38(1H,dt,J=8.3, 1.5), 7.86(1H,dd,J=7.8, 1.5).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for four hours
  3. washThe insoluble material was rinsed with methylene chloride
  4. customAll decanted solutions
  5. customthe organic layer separated
  6. extractionThe aqueous layer was extracted again with methylene chloride
  7. washthe combined organics washed once with brine
  8. dry with materialAfter drying over magnesium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-2ed0df190cd5455487c3578b4184f8be
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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