Tetrahydrofuran → HCID 15005393, compound

HRID 1460299Notes

Reaction equation

HRID 1460299 reaction equation
O.[NH2:2][NH2:3].[C:4]([C:6]1[CH:15]=[CH:14][C:9]([NH:10][C:11](=S)[CH3:12])=[CH:8][CH:7]=1)#[N:5].[CH2:16]1[CH2:20]OCC1>>[C:4]([C:6]1[CH:15]=[CH:14][C:9]([N:10]2[C:20]([CH3:16])=[N:3][N:2]=[C:11]2[CH3:12])=[CH:8][CH:7]=1)#[N:5]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 15005392HCID 15005392, compound

Product 1

HCID 15005393HCID 15005393, compound

Conditions

Temperature
80 °C

Procedure

Hydrazine hydrate (1.64 ml, 34 mmol) was added dropwise to a solution of p-cyanothioacetanilide prepared according to J. Pharm. Soc. Jpn., 1952, 72, 739 (5.43 gm, 30.9 mmol) in THF (50 ml) at room temperature. After 30 minutes, the solution was concentrated under reduced pressure and the residue treated with triethyl orthoacetate (40 ml). The mixture was heated at 80° C. for 30 minutes, cooled and the excess reagent was removed under reduced pressure. The residue was treated with ice-cold dilute aqueous ammonia (100 ml) and the product was filtered off, washed with water and dried in vacuo. The title triazole (4.85 g) was an off-white solid, m.p.>230° C.

Workup

  1. customprepared
  2. customat room temperature
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionthe residue treated with triethyl orthoacetate (40 ml)
  5. temperaturecooled
  6. customthe excess reagent was removed under reduced pressure
  7. additionThe residue was treated with ice-cold dilute aqueous ammonia (100 ml)
  8. filtrationthe product was filtered off
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-fa5ffa06e0474bab9d2f695b9126a196
Source dataset
uspto-grants-1991_12
Patent number
US05070205

Reaction notes

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