Isopropylamine → N-isopropyl-2-nitrobenzenesulfonamide

HRID 1893496Notes

Reaction equation

HRID 1893496 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21](Cl)(=[O:23])=[O:22])([O-:14])=[O:13]>ClCCl.C(OCC)(=O)C.CCCCCC>[CH:1]([NH:4][S:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N+:12]([O-:14])=[O:13])(=[O:22])=[O:23])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 4154456N-isopropyl-2-nitrobenzenesulfonamideYield 96.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Isopropylamine (11.07 g, 68.85 mmol) and triethylamine (13 ml, 93 mmol) were dissolved in dichloromethane (50 ml) and the mixture was stirred under ice-cooling. Thereto was added 2-nitrobenzenesulfonyl chloride (10.11 g, 45.62 mmol), and the mixture was stirred at room temperature for 6 hr. The reaction mixture was diluted with ethyl acetate-hexane=1:1 mixed solvent, and the organic layer was washed with diluted hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, the solution was concentrated under reduced pressure and the obtained solid was washed with hexane and air-dried to give the title compound (10.73 g, yield 96%) as a colorless solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 6 hr
  3. washthe organic layer was washed with diluted hydrochloric acid and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. washthe obtained solid was washed with hexane
  8. customair-dried

Sources & evidence

ORD record
ord-5862b5b77e1b473489a7e41129c6ad57
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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