Sulfuric Acid → trans-5-Methyl-3-p-cyanostyryl-1,2,4-oxadiazole

HRID 596781Notes

Reaction equation

HRID 596781 reaction equation
N([O-])=O.[Na+].[CH3:5][C:6]1[O:10][N:9]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16](N)=[CH:15][CH:14]=2)[N:7]=1.S(=O)(=O)(O)O.[C-:25]#[N:26].[K+]>O>[CH3:5][C:6]1[O:10][N:9]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([C:25]#[N:26])=[CH:15][CH:14]=2)[N:7]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 23668193Sodium NitriteHCID 68125323trans-5-Methyl-3-p-aminostyryl-1,2,4-oxadiazole

Product 1

HCID 68124994trans-5-Methyl-3-p-cyanostyryl-1,2,4-oxadiazoleYield 29.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (0.80g) in water (3 ml) was added during 20 min. to a stirred suspension of trans-5-methyl-3-p-aminostyryl-1,2,4-oxadiazole (2.01g) in 2N-sulphuric acid (20 ml) at 5°. The solution was maintained at 10° for one hour and then added during 30 min. to a solution of cuprous cyanide (1.01g) and potassium cyanide (2.28g) in water (8 ml) at 35°. The mixture was then heated to 70° when nitrogen ceased to be evolved. The cooled reaction mixture was filtered and the solid was washed with water and dried. The solid was triturated with boiling chloroform (150 ml) and the chloroform solution was evaporated under reduced pressure to give an orange solid which was recrystallised from ethanol (15 ml) with charcoal decolourisation to give title compound 0.62g (29.5%), m.p. 162°-163°, λmax. (EtOH) 288 nm, ε 32,300, νmax (CHBr3) 2250, (CN) 972 cm.-1 (trans CH=CH), τ (CDCl3) values include 2.27 and 2.87 (AB quartet, J = 16; trans CH=CH) and 7.36 (CH3).

Workup

  1. temperatureThe solution was maintained at 10° for one hour
  2. temperatureThe mixture was then heated to 70° when nitrogen
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. washthe solid was washed with water
  6. customdried
  7. customThe solid was triturated with boiling chloroform (150 ml)
  8. customthe chloroform solution was evaporated under reduced pressure
  9. customto give an orange solid which
  10. customwas recrystallised from ethanol (15 ml) with charcoal decolourisation

Sources & evidence

ORD record
ord-7efe35a2589e4ba8a8bc2998cbb51fdd
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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