Hydrochloric Acid → HCID 178515926, compound

HRID 26662Notes

Reaction equation

HRID 26662 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]=[C:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH:8]=[C:7]1/[CH:16]=[CH:17]/[C:18]#[N:19].[N-:20]=[N+:21]=[N-:22].[Na+].Cl>O1CCCC1>[O:5]=[C:6]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH:8]=[C:7]1/[CH:16]=[CH:17]/[C:18]1[NH:22][N:21]=[N:20][N:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 12330012trans-3-(4-oxo-4H-1-benzopyran-3-yl)-acrylonitrile

Product 1

HCID 178515926HCID 178515926, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under stirring, 4.6 parts of anhydrous aluminum chloride are added to 100 volume parts of dry tetrahydrofuran, followed by the addition of 3.11 parts of trans-3-(4-oxo-4H-1-benzopyran-3-yl)-acrylonitrile and 4.5 parts of sodium azide. The whole mixture is refluxed for 28 hours and, then, 35 volume parts of 15 weight% hydrochloric acid are added to the resulting mixture, followed by distilling off tetrahydrofuran under reduced pressure. The resulting residue is recovered by filtration and recrystallized from methanol, dimethylformamide-water and, then, from methanol. This procedure yields trans-1-(4-oxo-4H-1-benzopyran-3-yl)-2-(1H-tetrazol-5-yl) ethylene as light-yellow needles. Melting point: 254.5°-255° C.(decomp. with foaming).

Workup

  1. temperatureThe whole mixture is refluxed for 28 hours
  2. distillationby distilling off tetrahydrofuran under reduced pressure
  3. filtrationThe resulting residue is recovered by filtration
  4. customrecrystallized from methanol, dimethylformamide-water

Sources & evidence

ORD record
ord-d08d479268884998901ac9c819611fbe
Source dataset
uspto-grants-1979_04
Patent number
US04151180

Reaction notes

Loading…