Sodium Chloride → 4-Methyl-2-(pyridin-3-yl)-1,3-thiazole-5-amine

HRID 1182777Notes

Reaction equation

HRID 1182777 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:5][C:6]=1[N+:7]([O-])=O.[Sn](Cl)Cl.C(OC)(C)(C)C.[Cl-].[Na+]>Cl.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:5][C:6]=1[NH2:7]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 15413tert-Butyl methyl etherHCID 24479Stannous ChlorideHCID 2176783-(4-Methyl-5-nitro-1,3-thiazol-2-yl)pyridine

Product 1

HCID 666453454-Methyl-2-(pyridin-3-yl)-1,3-thiazole-5-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

10.1 g (45.6 mmol) of 3-(4-methyl-5-nitro-1,3-thiazol-2-yl)pyridine (for preparation see DE 2221647) were dissolved in 100 ml of 10% hydrochloric acid together with 10 ml of conc. hydrochloric acid, and 25 g of tin(II) chloride dissolved in 10% hydrochloric acid were added in portions, and the mixture was stirred for 1 h (hour), in the course of which heating occurred. The mixture was poured into ice/sodium hydroxide solution, methyl t-butyl ether, ethyl acetate and saturated sodium chloride solution were added, the mixture was extracted 4 times at pH=10 with ethyl acetate, the combined organic phases were dried with Mg504 and the mixture was concentrated. The residue was recrystallized from benzotrifluoride.

Workup

  1. additionwere added in portions
  2. temperaturein the course of which heating
  3. additionwere added
  4. extractionthe mixture was extracted 4 times at pH=10 with ethyl acetate
  5. customthe combined organic phases were dried with Mg504
  6. concentrationthe mixture was concentrated
  7. customThe residue was recrystallized from benzotrifluoride

Sources & evidence

ORD record
ord-9806e7f9369644d3860d55efa75ff097
Source dataset
uspto-grants-2014_03
Patent number
US08664229B2

Reaction notes

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