Stannous Chloride → HCID 67333977, compound

HRID 1896744Notes

Reaction equation

HRID 1896744 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>C(O)C>[C:16]1([CH3:19])[CH:15]=[CH:14][C:13]([C:11]2[O:12][C:8]3[C:9](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=3)[N:10]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 67331593HCID 67331593, compound

Product 1

HCID 67333977HCID 67333977, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To 4-nitro-2-p-tolylbenzo[d]oxazole (330 mg, 1.30 mmol) in ethanol (20 mL) was added tin (II) chloride (1.23 g, 6.5 mmol). The suspension was stirred at 70° C. for 16 h. After cooling, the solution was poured into ice/water and neutralize with saturated aqueous NaHCO3. The aqueous layer was then extracted twice with ethyl acetate (500 mL). The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 188 mg (65%) of the title compound (LCMS RT=6.76 min, MH+ 225.1)

Workup

  1. temperatureAfter cooling
  2. extractionThe aqueous layer was then extracted twice with ethyl acetate (500 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-8d5c66c5ed7e4cdd90ce4459406ffa42
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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