Stannous Chloride → [3-(2-Pyridin-3-yl-1,3-thiazol-4-yl)phenyl]amine

HRID 1977751Notes

Reaction equation

HRID 1977751 reaction equation
Br.[N+:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1)([O-])=O.[Sn](Cl)Cl>C(O)C.Cl>[NH2:2][C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 24479Stannous Chloride2×HCID 28238744-(3-Nitrophenyl)-2-(3-pyridyl)-thiazole hydrobromide

Product 1

HCID 22724371[3-(2-Pyridin-3-yl-1,3-thiazol-4-yl)phenyl]amineYield 85%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 4-(3-nitrophenyl)-2-(3-pyridyl)-thiazole hydrobromide (3.6 g, 10 mmol) in ethanol (150 ml) was treated with a solution of tin (II) chloride (3.7 g, 30 mmol) in concentrated hydrochloric acid (12 ml). The mixture was heated at 50° C. for 16 h. A further portion of tin (II) chloride (2.9 g, 15 mmol) was added and the mixture heated at 50° C. for a further 4 hours before being evaporated to dryness. The residue was partitioned between ethyl acetate and 1M aqueous sodium hydroxide. The ethyl acetate extract was dried (Na2SO4) and filtered through a plug of silica. Evaporation afforded the title compound as a yellow solid (2.15 g, 85%).

Workup

  1. temperaturethe mixture heated at 50° C. for a further 4 hours
  2. custombefore being evaporated to dryness
  3. customThe residue was partitioned between ethyl acetate and 1M aqueous sodium hydroxide
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered through a plug of silica
  7. customEvaporation

Sources & evidence

ORD record
ord-18c131c991234916bc219bb6208cbe10
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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