Hydrochloric Acid → HCID 178527130, compound

HRID 485432Notes

Reaction equation

HRID 485432 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[S:12](=[O:22])(=[O:21])[C:11]=2[CH:23]=1)#[N:6].[N-:24]=[N+:25]=[N-:26].[Na+].Cl>O1CCCC1>[NH:24]1[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[CH2:16][CH2:15][C:14]4[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=4[S:12](=[O:21])(=[O:22])[C:11]=3[CH:23]=2)=[N:6][N:26]=[N:25]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 20270239HCID 20270239, compound

Product 1

HCID 178527130HCID 178527130, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 9 cc. tetrahydrofuran, cooled in an ice bath, is added in the following order 862 mg. aluminum chloride, 792 mg. 3-cyano-10,11-dihydrodibenzo[b,f]thiepin-5,5-dioxide, and 839 mg. sodium azide. The mixture is refluxed for six hours, cooled down, treated with 3 cc. 15% aqueous hydrochloric acid. The organic solvent is decanted and the residue triturated several times with ethyl acetate. The combined organic phases are washed with water, then extracted with aqueous sodium bicarbonate solution. The aqueous layer is acidified with hydrochloric acid and the precipitated tetrazole is filtered, washed with water, and dried, yield 580 mg. (63%), m.p. 233° C. dec.

Workup

  1. additionis added in the following order 862 mg
  2. temperatureThe mixture is refluxed for six hours
  3. temperaturecooled down
  4. additiontreated with 3 cc
  5. customThe organic solvent is decanted
  6. customthe residue triturated several times with ethyl acetate
  7. washThe combined organic phases are washed with water
  8. extractionextracted with aqueous sodium bicarbonate solution
  9. filtrationthe precipitated tetrazole is filtered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-37247cc0e1224818ada5cb4aa0de37de
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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