Dimethylamine → 2-cyano-N,N-dimethylbenzenesulfonamide

HRID 1015900Notes

Reaction equation

HRID 1015900 reaction equation
[CH3:1][NH:2][CH3:3].C(N(CC)CC)C.[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20])#[N:12]>O1CCCC1>[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([N:2]([CH3:3])[CH3:1])(=[O:21])=[O:20])#[N:12]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 5223472-Cyanobenzenesulfonyl Chloride

Product 1

HCID 6978732-cyano-N,N-dimethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Step 1) To a mixture of dimethylamine (49.6 ml, 2M tetrahydrofuran solution) and triethylamine (3.46 ml) was added a solution of 2-cyanobenzene-1-sulfonyl chloride (5.0 g) in tetrahydrofuran (20 ml) at room temperature. The mixture was stirred at the same temperature for 2 hr, and concentrated under reduced pressure. The residue was suspended in water, and filtered. The filtered solid was dissolved in dichloromethane, the solution was washed with water, and the organic layer was dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to give 2-cyano-N,N-dimethylbenzenesulfonamide (5.1 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationfiltered
  3. dissolutionThe filtered solid was dissolved in dichloromethane
  4. washthe solution was washed with water
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-f838144794b5476b990c71e36340806a
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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