Dimethylformamide dimethyl acetal → 5-chloro-N-[dimethylamino-methylene]-pentane-sulfonamide

HRID 742948Notes

Reaction equation

HRID 742948 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15]([NH2:18])(=[O:17])=[O:16].S([O-])(O)(=O)=O.[Na+]>CN(C)C=O>[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15]([N:18]=[CH:3][N:4]([CH3:6])[CH3:5])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 516919Sodium BisulfateHCID 99899625-Chloropentanesulfonamide

Product 1

HCID 545132785-chloro-N-[dimethylamino-methylene]-pentane-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.29 ml of N,N-dimethylformamide-dimethyl acetal were added dropwise at ambient temperature under an inert gas atmosphere to a solution of 1.5 g of the product of Step A in 8 ml of dimethylformamide. The solution was stirred at ambient temperature for 3 hours, then poured into a 1% aqueous solution of sodium hydrogen sulfate, extracted with ethyl acetate, washed with water, then with a saturated aqueous solution of sodium chloride, dried and evaporated to dryness under reduced pressure to obtain 1.809 g of the expected product.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8e0cd1547464457aa90af5a7bc8db1af
Source dataset
uspto-grants-1996_09
Patent number
US05556845

Reaction notes

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