Stannous Chloride → 3-(2,6-Dichlorophenyl)-5-(3-aminophenyl)-1,2,4-oxadiazole

HRID 1883219Notes

Reaction equation

HRID 1883219 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=2)[O:11][N:10]=1.O.O.[Sn](Cl)Cl.[Sn](Cl)Cl>C(OCC)(=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)[O:11][N:10]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 61436Stannous chloride dihydrateHCID 113596083-(2,6-Dichlorophenyl)-5-(3-nitrophenyl)-1,2,4-oxadiazole

Product 1

HCID 114609353-(2,6-Dichlorophenyl)-5-(3-aminophenyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The nitro oxadiazole prepared in Step 1 (200 mg) was dissolved in ethyl acetate (20 mL) and tin (II) chloride dihydrate (162 mg, 1.2 molar equivalent) was added. The mixture was stirred at room temperature for 1 h. An additional 1.2 molar equivalents of tin (II) chloride was added. After a further 4 h at room temperature, the reaction mixture was diluted with ethyl acetate and washed three times with water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the desired 3-(2,6-dichlorophenyl)-5-(3-aminophenyl)-1,2,4-oxadiazole as a white solid in quantitative yield. NMR (300 MHz, DMSO-d6): 7.70 (m, 3H), 7.36 (s, 1H), 7.24 (d, 2H), 6.91 (m, 1H), 5.57 ppm (broad s, 2H). LC-MS tr=33.1 min (Method W) MH+=307

Workup

  1. waitAfter a further 4 h at room temperature
  2. washwashed three times with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-634ea17398fb4937a9657f328f9f53a5
Source dataset
uspto-grants-2004_07
Patent number
US06759538B2

Reaction notes

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