Ammonium Chloride → 4-[beta-(Methylthio)ethylamino]aniline

HRID 1111267Notes

Reaction equation

HRID 1111267 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:16]=[CH:15][C:9]([NH:10][CH2:11][CH2:12][S:13][CH3:14])=[CH:8][CH:7]=1)([O-])=O>[Zn]>[CH3:14][S:13][CH2:12][CH2:11][NH:10][C:9]1[CH:15]=[CH:16][C:6]([NH2:3])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 14646022N-[2-(Methylsulfanyl)ethyl]-4-nitroaniline

Product 1

HCID 146460234-[beta-(Methylthio)ethylamino]aniline

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

0.8 g of ammonium chloride and 20 g of powdered zinc are added to 44 ml of aqueous-alcoholic solution (10% of water, 90% of alcohol). This mixture is brought to reflux with stirring, and 0.04 mole (8.5 g) of 4-nitro-N-[β-(methylthio)ethyl]aniline is added, the addition being regulated so as to maintain the reflux without heating. The decolorized reaction medium is filtered while boiling into a flask containing 8.5 ml of 36% strength hydrochloric acid. The expected product precipitates in the form of a dihydrochloride. It is dried under vacuum at 55° C.

Workup

  1. temperatureto reflux
  2. additionthe addition
  3. temperatureto maintain the
  4. temperaturereflux
  5. temperaturewithout heating
  6. customThe decolorized reaction medium
  7. filtrationis filtered
  8. customwhile boiling into a flask
  9. additioncontaining 8.5 ml of 36% strength hydrochloric acid
  10. customThe expected product precipitates in the form of a dihydrochloride
  11. customIt is dried under vacuum at 55° C.

Sources & evidence

ORD record
ord-c8e6700e8e0d4100a2335bb780b6e9a3
Source dataset
uspto-grants-1990_12
Patent number
US04979961

Reaction notes

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