Ammonium Chloride → HCID 3026819, compound

HRID 1162734Notes

Reaction equation

HRID 1162734 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.[NH4+].[Cl-]>C(O)C.[Fe]>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([NH2:16])=[C:9]([S:8][C:1]2[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 561412HCID 561412, compound

Product 1

HCID 3026819HCID 3026819, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 1.8 g of 2-benzylthio-4-chloro-nitrobenzene in 100 ml ethanol was added 2 g powdered iron and 20 mL of 0.33N NH4Cl. The mixture was heated at 70° C. for 6 hr. The mixture was cooled and filtered through a pad of Celite. The filtrate was condensed and purified by flash chromatography (hexane/ethyl acetate 4:1 as eluent) to yield 1.25 g of an oil. LC-MS showed a single peak with the expected (M+H+) of 236.

Workup

  1. additionwas added 2 g
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through a pad of Celite
  4. customcondensed
  5. custompurified by flash chromatography (hexane/ethyl acetate 4:1 as eluent)

Sources & evidence

ORD record
ord-36b5a5bc1bd54875bee9b5b25cc24ee8
Source dataset
uspto-grants-2010_10
Patent number
US07820717B2

Reaction notes

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