Tetrahydrofuran → 3-amino-N-cyclopropylbenzenesulfonamide

HRID 1792502Notes

Reaction equation

HRID 1792502 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH:14]1([NH2:17])[CH2:16][CH2:15]1.O1CCCC1>O>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([NH:17][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 84763-Nitrobenzenesulfonyl chlorideHCID 69828Cyclopropylamine

Product 1

HCID 53030613-amino-N-cyclopropylbenzenesulfonamideYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g 3-nitrobenzene sulfonyl chloride, 1.8 g cyclopropyl amine and 50 mL tetrahydrofuran was stirred for 30 minutes under ice-cooling. Water was added to the mixture which was then extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, then the residue was dissolved in 100 mL solvent mixture of tetrahydrofuran and methanol, 50 mg of 10% palladium-carbon was added thereto, and the mixture was hydrogenated at ordinary pressure for 12 hours. The reaction mixture was filtered through Celite, and the solvent was evaporated, whereby 1.5 g of the title compound was obtained as a pale yellow solid.

Workup

  1. temperaturecooling
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in 100 mL solvent mixture of tetrahydrofuran and methanol, 50 mg of 10% palladium-carbon
  7. additionwas added
  8. waitthe mixture was hydrogenated at ordinary pressure for 12 hours
  9. filtrationThe reaction mixture was filtered through Celite
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-55df594452ee4740a10f16d5383c63b8
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

Loading…