Stannous Chloride → HCID 58710057, compound

HRID 2375902Notes

Reaction equation

HRID 2375902 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([C:11]2[S:15][CH:14]=[N:13][CH:12]=2)[C:3]1=[O:16].Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(O)C>[NH2:8][C:6]1[CH:5]=[C:4]([C:11]2[S:15][CH:14]=[N:13][CH:12]=2)[C:3](=[O:16])[N:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 58710056HCID 58710056, compound

Product 1

HCID 58710057HCID 58710057, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-methyl-5-nitro-3-thiazol-5-yl-1H-pyridin-2-one (290 mg, 1.22 mmol) in ethanol (10 mL) was added SnCl2 (2.342 g, 12.22 mmol). The mixture was stirred at 90° C. for 15 h. After cooled to rt, sat. NaHCO3 (aq) was added dropwise to the reaction to adjust the pH to 9-10. The resulting solution was filtered through a Celite pad. The filtrate was concentrated to dryness in vacuo to afford the crude product, which was used directly in the next step without purification. MS (ES+): m/z 208.21 [MH+]. HPLC: tR=1.47 min (ZQ2000, polar—5 min).

Workup

  1. temperatureAfter cooled to rt
  2. filtrationThe resulting solution was filtered through a Celite pad
  3. concentrationThe filtrate was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-2688fb3b317f4f14a0732b05bc25583b
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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