Stannous Chloride → 5-Amino-2-(3-pyridinyl)benzothiazole

HRID 1287831Notes

Reaction equation

HRID 1287831 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:9][C:8]=2[CH:18]=1)([O-])=O.Cl[Sn]Cl>Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:9][C:8]=2[CH:18]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 127819025-Nitro-2-(pyridin-3-yl)-1,3-benzothiazole

Product 1

HCID 215067025-Amino-2-(3-pyridinyl)benzothiazoleYield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

5-Nitro-2-(3-pyridinyl)benzothiazole 11.2 g, 0.044 mole, is dissolved in 45 cc of concentrated HCl. SnCl2, 35 g, in 45 cc of concentrated HCl is added, and the resulting mixture heated for 1 hour on a steam bath. After cooling, the precipitate is filtered, washed in cold HCl and neutralized in cold NaOh solution. The amine is filtered, washed with H2O and dried to yield 8.0 g of product m.p. 189°-196°.

Workup

  1. temperaturethe resulting mixture heated for 1 hour on a steam bath
  2. temperatureAfter cooling
  3. filtrationthe precipitate is filtered
  4. washwashed in cold HCl and neutralized in cold NaOh solution
  5. filtrationThe amine is filtered
  6. washwashed with H2O
  7. customdried

Sources & evidence

ORD record
ord-d1089cec0c884777857300f2018536c3
Source dataset
uspto-grants-1976_10
Patent number
US03985885

Reaction notes

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