Water → HCID 178440789, compound

HRID 1078206Notes

Reaction equation

HRID 1078206 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[CH:8]=[C:9]1[C:14](=[O:15])[N:13]([CH2:16][C:17]#[N:18])[C:12]2[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=2[S:10]1)([CH3:4])([CH3:3])[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+].O>CC(C)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=1[OH:26])[CH:8]=[C:9]1[C:14](=[O:15])[N:13]([CH2:16][C:17]2[NH:33][N:32]=[N:31][N:18]=2)[C:12]2[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=2[S:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 54061185HCID 54061185, compound

Product 1

HCID 178440789HCID 178440789, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 2-(3,5-di-tert.-butyl-4-hydroxybenzylidene) -4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (compound No. 1-1, 0.335 g) in dimethylformaldehyde (5 ml), sodium azide (0.078 g) and ammonium chloride (0.064 g) were added. The mixture was stirred overnight at 105° C. under a nitrogen atmosphere. To the mixture, water was added, and the whole was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. To the oily residue, 1N aqueous sodium hydroxide solution was added. The mixture was washed with diethyl ether, acidified with 2N hydrochloric acid and 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 0.21 g (56.9%) of the titled compound.

Workup

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

Sources & evidence

ORD record
ord-4abd2381923847feab648a528e381c46
Source dataset
uspto-grants-1996_08
Patent number
US05547952

Reaction notes

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