Hydrochloric Acid → HCID 2836736, compound

HRID 1012302Notes

Reaction equation

HRID 1012302 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16].Cl>C(Cl)(Cl)Cl>[C:15]([NH:19][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)(=[O:10])=[O:9])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 5606384-Methyl-3-nitrobenzenesulfonyl chloride

Product 1

HCID 2836736HCID 2836736, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-methyl-3-nitrobenzenesulfonyl chloride (5.40 g, 22.9 mmol) in chloroform (50 ml) was added tert-butylamine (6.00 ml, 57.1 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and hexane was added to the residue. The precipitated solid was collected by filtration and dried in vacuo to give N-tert-butyl-4-methyl-3-nitrobenzenesulfonamide (5.89 g, yield 94.6%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure, and hexane
  7. additionwas added to the residue
  8. filtrationThe precipitated solid was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-0768500b70a1478b9785b10d729717e9
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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