3-o-Nitrostyryl-1,2,4-oxadiazole → trans-3-o-Aminostyryl-1,2,4-oxadiazole

HRID 596778Notes

Reaction equation

HRID 596778 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[CH:6]=[CH:7][C:8]1[N:12]=[CH:11][O:10][N:9]=1)([O-])=O>CC(C)=O.[Cl-].[Cl-].[Ti+2]>[NH2:1][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1/[CH:6]=[CH:7]/[C:8]1[N:12]=[CH:11][O:10][N:9]=1

Participants

4

Reactant 1

HCID 542282073-o-Nitrostyryl-1,2,4-oxadiazole

Product 1

HCID 68125074trans-3-o-Aminostyryl-1,2,4-oxadiazoleYield 80.2%

Reagents, catalysts & solvents 2

HCID 10290777Titanium(2+);dichlorideCatalystHCID 180AcetoneSolvent

Procedure

Titanous chloride solution (15% w/v, 380 ml.) was added during 25 min. to a stirred solution of 3-o-nitrostyryl-1,2,4-oxadiazole (10.85 g.) in acetone (1 litre). After 30 min. more, the acetone was removed, and solid sodium hyrdogen carbonate was added to the stirred solution until the pH was 6-7. The mixture was extracted thoroughly with ethyl acetate solution was washed with water, then dried (MgSO4) and evaporated, leaving trans-3-o-aminostyryl-1,2,4-oxadiazole (7.5 g., 80%), m.p. 108°- 109°, λmax. 240, 280- 281, 350 nm, ε 14000, 12800, 6200 [Found (after sublimation): C, 64.2; H, 5.2; N, 22.1 C10H9N3O requires C, 64.2; H, 4.85; N, 22.45%].

Workup

  1. customthe acetone was removed
  2. additionsolid sodium hyrdogen carbonate was added to the stirred solution until the pH was 6-7
  3. extractionThe mixture was extracted thoroughly with ethyl acetate solution
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-ae82459d1b3e43fb9d6f865f2ef49c4c
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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