Dimethylformamide dimethyl acetal → HCID 54369360, compound

HRID 1382996Notes

Reaction equation

HRID 1382996 reaction equation
[S:1]([C:5]1[O:13][C:12]2[CH:11]=[C:10]([CH3:14])[N:9]=[CH:8][C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>C(#N)C.C(Cl)(Cl)Cl>[CH3:17][N:18]([CH3:20])[CH:19]=[N:2][S:1]([C:5]1[O:13][C:12]2[CH:11]=[C:10]([CH3:14])[N:9]=[CH:8][C:7]=2[CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 14372112HCID 14372112, compound

Product 1

HCID 54369360HCID 54369360, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-sulfamoyl-6-methylfuro[3,2-c]pyridine (3.65 g, 17.2 mmol) in acetonitrile (80 ml), under a nitrogen atmosphere, was added N,N-dimethylformamide dimethyl acetal (2.6 ml, 19.6 mmol). This reaction was stirred for 1.5 hours at room temperature and then diluted with chloroform and washed with water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered through a charcoal pad and the solvent evaporated. The residue was triturated with diethyl ether and the product collected (4.31 g, 93% yield) and used as is. A small portion was crystallized from ethyl acetate for microanalysis, mp. 175°-177° C.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through a charcoal pad
  5. customthe solvent evaporated
  6. customThe residue was triturated with diethyl ether
  7. customthe product collected (4.31 g, 93% yield)
  8. customA small portion was crystallized from ethyl acetate for microanalysis, mp. 175°-177° C.

Sources & evidence

ORD record
ord-0a3a95a9770240ec8dcb1786755f6b60
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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