Hydrochloric Acid → HCID 16722586, compound

HRID 2421102Notes

Reaction equation

HRID 2421102 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)=[N:16][N:17]=1.Cl.O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[O:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])=[N:16][N:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 61436Stannous chloride dihydrateHCID 67214857HCID 67214857, compound

Product 1

HCID 16722586HCID 16722586, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 2-(5-methyl-3-phenyl-isoxazol-4-yl)-5-(2-nitro-phenyl)-[1,3,4]oxadiazole (2.20 g, 63.2 mmol) in ethanol (100 mL) was added under a nitrogen atmosphere aqueous HCl (1 M, 7.6 mL, 76 mmol) and tin(II) chloride dihydrate (7.13 g, 31.6 mmol). The reaction mixture was then stirred for 2 h at 90° C., cooled to ambient temperature and poured onto an aqueous solution of sodium carbonate (saturated, 50 mL) and ethyl acetate (100 mL), stirred for 1 h and was filtered over Hyflo®. The Hyflo® was then washed with ethyl acetate (500 mL) and the aqueous phase extracted with ethyl acetate (100 mL). Drying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate 95:5 to 50:50) afforded the title compound (564 mg, 28%) as a white solid. MS: m/e=319.1 [M+H]+.

Workup

  1. temperaturecooled to ambient temperature
  2. stirringstirred for 1 h
  3. filtrationwas filtered over Hyflo®
  4. washThe Hyflo® was then washed with ethyl acetate (500 mL)
  5. extractionthe aqueous phase extracted with ethyl acetate (100 mL)
  6. dry with materialDrying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate 95:5 to 50:50)

Sources & evidence

ORD record
ord-c5fd62e253b7482abab401d3af680e37
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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