Ammonium Chloride → 5-Amino-6-(2-thiazolylthio)-1-indanone

HRID 1654784Notes

Reaction equation

HRID 1654784 reaction equation
[Cl-].[NH4+].C1O[C:6]2([C:14]3[C:9](=[CH:10][C:11]([N+:21]([O-])=O)=[C:12]([S:15][C:16]4[S:17][CH:18]=[CH:19][N:20]=4)[CH:13]=3)[CH2:8][CH2:7]2)[O:5]C1>C(O)C.O.[Fe]>[NH2:21][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][C:12]=1[S:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)[C:6](=[O:5])[CH2:7][CH2:8]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 108543455-Nitro-6-(2thiazolylthio)-1-indanone ethylene acetal

Product 1

HCID 105634525-Amino-6-(2-thiazolylthio)-1-indanoneYield 69.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron powder (265 mg, 4.7 mmol), ammonium chloride (35 mg, 0.65 mmol) and the nitroindane from Step 7 (275 mg, 0.82 mmol) were mixed together in ethanol (5 ml) and water (2.5 mL). The mixture was refluxed for l h and then filtered through celite, washing the cake with EtOAc. The volatile, s were removed in vacuo and the residue was dissolved in EtOAc:CH2Cl2 (3:1), washed with brine and dried over MgSO4. Evaporation of the solvent left a residue that was purified by flash chromatography on silica gel (EtOAc:toluene:CH2Cl2 from 30:50:20 to 1:1:1 ) to give 150 mg of the title compound.

Workup

  1. temperatureThe mixture was refluxed for l h
  2. filtrationfiltered through celite
  3. washwashing the cake with EtOAc
  4. customThe volatile, s were removed in vacuo
  5. dissolutionthe residue was dissolved in EtOAc:CH2Cl2 (3:1)
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent
  9. waitleft a residue that
  10. customwas purified by flash chromatography on silica gel (EtOAc:toluene:CH2Cl2 from 30:50:20 to 1:1:1 )

Sources & evidence

ORD record
ord-5f5ef7d22fbf4fc79a07c5877d24ad5b
Source dataset
uspto-grants-1995_04
Patent number
US05409944

Reaction notes

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