Ammonium Chloride → 3-Amino-4-[(3-chloropyrazin-2-yl)thio]benzyl alcohol

HRID 1059293Notes

Reaction equation

HRID 1059293 reaction equation
[Cl:1][C:2]1[C:3]([S:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=2[N+:17]([O-])=O)=[N:4][CH:5]=[CH:6][N:7]=1.[Cl-].[NH4+]>O1CCCC1.CC(O)C.O.[Fe]>[NH2:17][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[S:8][C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=1)[CH2:13][OH:14]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 114379644-[(3-Chloropyrazin-2-yl)thio]-3-nitrobenzyl alcohol

Product 1

HCID 235641353-Amino-4-[(3-chloropyrazin-2-yl)thio]benzyl alcoholYield 102.2%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.60 g of 4-[(3-chloropyrazin-2-yl)thio]-3-nitrobenzyl alcohol was dissolved in a solvent mixture of tetrahydrofuran (20 ml)/2-propanol (20 ml)/water (7 ml). After adding 0.16 g of ammonium chloride and 1.50 g of iron powder, the resulting mixture was heated under reflux for 30 minutes. Then the reaction mixture was filtered through celite and concentrated under reduced pressure. After adding ethanol, the reaction mixture was concentrated under reduced pressure. Then tetrahydrofuran was added to the residue and the insoluble matters were separated by filtration. After distilling off the solvent under reduced pressure, 1.47 g of the title compound was obtained as yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationThen the reaction mixture was filtered through celite and
  4. concentrationconcentrated under reduced pressure
  5. additionAfter adding ethanol
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionThen tetrahydrofuran was added to the residue
  8. customthe insoluble matters were separated by filtration
  9. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-9374dddd8b6943478e4aa9e8b249cda0
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…