Hydrochloric Acid → HCID 178438910, compound

HRID 1078207Notes

Reaction equation

HRID 1078207 reaction equation
C([O:4][C:5]1[C:25]([CH:26]([CH3:28])[CH3:27])=[CH:24][C:8]([CH:9]=[C:10]2[C:15](=[O:16])[N:14]([CH2:17][C:18]#[N:19])[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[S:11]2)=[CH:7][C:6]=1[CH:29]([CH3:31])[CH3:30])(=O)C.[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].Cl.[Cl-].[Na+]>CC(C)=O>[OH:4][C:5]1[C:6]([CH:29]([CH3:31])[CH3:30])=[CH:7][C:8]([CH:9]=[C:10]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[NH:34][N:33]=[N:32][N:19]=3)[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[S:11]2)=[CH:24][C:25]=1[CH:26]([CH3:28])[CH3:27]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 53932584HCID 53932584, compound

Product 1

HCID 178438910HCID 178438910, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 2-(4-acetoxy-3,5-diisopropylbenzylidene)-4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (compound No. 1-3, 0.47 g) in dimethylformaldehyde (5 ml), sodium azide (0.21 g) and ammonium chloride (0.17 g) were added. The mixture was stirred overnight at 105° C. under a nitrogen atmosphere. To acidify the mixture, 1N hydrochloric acid was added. Saturated sodium chloride solution was added to the mixture and the whole was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. To the residue, 1N aqueous sodium hydroxide solution was added and the whole was washed with diethyleter. 5.8N hydrochloric acid was added to the aqueous layer to acidify it and the whole was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.36 g (76.4%) of the titled compound.

Workup

  1. additionwas added
  2. extractionthe whole was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. additionTo the residue, 1N aqueous sodium hydroxide solution was added
  6. washthe whole was washed with diethyleter
  7. addition5.8N hydrochloric acid was added to the aqueous layer
  8. extractionthe whole was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe oily residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-986bc99cb60040998b213c7fa53e7269
Source dataset
uspto-grants-1996_08
Patent number
US05547952

Reaction notes

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