Dimethylformamide dimethyl acetal → HCID 54386855, compound

HRID 569067Notes

Reaction equation

HRID 569067 reaction equation
[S:1]([C:5]1[S:13][C:12]2[C:7](=[N+:8]([O-:14])[CH:9]=[CH:10][CH:11]=2)[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>C(#N)C>[CH3:17][N:18]([CH3:20])[CH:19]=[N:2][S:1]([C:5]1[S:13][C:12]2[C:7](=[N+:8]([O-:14])[CH:9]=[CH:10][CH:11]=2)[CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 20148551HCID 20148551, compound

Product 1

HCID 54386855HCID 54386855, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a partial suspension of 2-sulfamoylthieno[3,2-b]pyridine-4-oxide (1.64 g, 7.1 mmol) in acetonitrile (45 ml), under a nitrogen atmosphere at room temperature was added dimethylformamide dimethyl acetal (1.5 ml, 11 mmol). The product began to precipitate after initial complete solution. After stirring for 18 hours, the reaction mixture was diluted with chloroform to dissolve the product. The solution was washed with water, dried over anhydrous sodium sulfate, filtered through charcoal and evaporated to give nearly pure product (1.9 g, 94% yield). Recrystallization from hot chloroform gave pure product (1.6 g), m.p. 224°-225.5° C.

Workup

  1. customto precipitate after initial complete solution
  2. additionthe reaction mixture was diluted with chloroform
  3. dissolutionto dissolve the product
  4. washThe solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through charcoal
  7. customevaporated

Sources & evidence

ORD record
ord-6ee763669e784df9bfde66bce083ebff
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

Loading…