Dimethylformamide dimethyl acetal → 2-Chloro-N-dimethylaminomethylene-5-formyl-benzenesulfonamide

HRID 2370731Notes

Reaction equation

HRID 2370731 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[S:10]([N:13]=[CH:16][N:17]([CH3:19])[CH3:18])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 146546022-Chloro-5-formylbenzene-1-sulfonamide

Product 1

HCID 539657862-Chloro-N-dimethylaminomethylene-5-formyl-benzenesulfonamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g (22.8 mmol) 2-Chloro-5-formyl-benzenesulfonamide were dissolved in 50 ml dichloromethane. 4.08 g (34.3 mmol) dimethylformamide dimethylacetal were added and the mixture was refluxed for 2 h. After cooling to room temperature, the solution was washed twice with H2O, dried over magnesium sulfate and evaporated. 5.16 g of the crude product were obtained and used in the next step without further purification. Rt=1.14 min (Method #1). Detected mass: 275.1/277.1 (M+H+).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. washthe solution was washed twice with H2O
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-866279e9037a4df9b575194b7f2c2221
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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