Propargyl bromide → N,N-Dimethyl-4-(2-propynylamino)benzenesulfonamide

HRID 1722710Notes

Reaction equation

HRID 1722710 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:14](Br)[C:15]#[CH:16].N1C(C)=CC=CC=1C>CN(C)C(=O)C>[CH3:12][N:11]([CH3:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:16][C:15]#[CH:14])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 79372,6-LutidineHCID 74369Benzenesulfonamide, 4-amino-N,N-dimethyl-

Product 1

HCID 14650034N,N-Dimethyl-4-(2-propynylamino)benzenesulfonamideYield 602.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Under an atmosphere of nitrogen gas, a mixture of 17 g (0.0085 mol) of 4-amino-N,N-dimethylbenzenesulfonamide, 25.5 ml (0.229 mol) of propargyl bromide, and 20.4 ml (0.175 mol) of 2,6-lutidine in 250 ml of N,N-dimethylacetamide is stirred at 90° for three and one-half hours, allowed to cool, and concentrated in vacuo. The concentrate is taken up in dichloromethane and water; the organic layer is separated, washed with brine, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed over 1.1 kg of silica gel with a gradient of ethyl acetate in toluene of 10 to 15% to give 12.2 g of product, Rf (10% methanol/dichloromethane)≃0.84. Recrystallization from ethanol affords 10.2 g (50%) of product, as off-white crystals; mp 128°-131° C.

Workup

  1. temperatureto cool
  2. concentrationconcentrated in vacuo
  3. customthe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed over 1.1 kg of silica gel with a gradient of ethyl acetate in toluene of 10 to 15%

Sources & evidence

ORD record
ord-e714b2bdd1e64ce492ccef5c6840c392
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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