Tin tetrachloride → HCID 82468131, compound

HRID 1508862Notes

Reaction equation

HRID 1508862 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C:9]2[O:10][CH:11]=[CH:12][N:13]=2)=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C.[OH-].[Na+]>[O:10]1[CH:11]=[CH:12][N:13]=[C:9]1[CH2:8][C:7]1[CH:14]=[CH:15][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 24287Tin tetrachlorideHCID 901105832-(4-Nitrobenzyl)oxazole

Product 1

HCID 82468131HCID 82468131, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(4-nitrobenzyl)oxazole (0.108 g, 0.59 mmol) in ethanol (3 mL) was added tin chloride (0.531 g, 2.35 mmol) and the mixture was stirred at 50° C. for 3 h. After this time, the reaction mixture was cooled, diluted with 1M sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to afford the title compound (0.076 g, 63%) as a yellow oil. MW=174.20. 1H NMR (CD3OD, 500 MHz) δ 7.78 (d, J=0.8 Hz, 1H), 7.05 (d, J=0.8 Hz, 1H), 7.02-6.97 (m, 2H), 6.69-6.65 (m, 2H), 3.97 (s, 2H); APCI MS m/z 175 [M+H]+.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7ecaa61db4b94a3287c53b43cfc33c08
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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