Potassium Hydroxide → HCID 13286106, compound

HRID 1463327Notes

Reaction equation

HRID 1463327 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O.[OH-].[K+]>Cl.C(O)C.O.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 14797Potassium HydroxideHCID 14555109HCID 14555109, compound

Product 1

HCID 13286106HCID 13286106, compoundYield 107.3%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 22.3 g of crude 4-nitro-N,N-dimethyl-benzenemethanesulfonamide (contaminated with dimethylamine hydrochloride as described above) in 45 mL of 2N hydrochloric acid, 100 mL of ethanol and 200 mL of water was added 5.0 g of 10% palladium on carbon. The mixture was hydrogenated in a Parr apparatus at 60 to 50 psi for three hours. The mixture was filtered and the ethanol removed in vacuo. The resulting aqueous solution was treated with 15% aqueous potassium hydroxide. Precipitate began forming at pH four. Addition of potassium hydroxide was continued until the pH had reached nine. The product was isolated by filtration and dried for sixteen hours at 65° C. at 0.05 mm Hg to give 21.0 g (83%, two steps) of 4-amino-N,N-dimethylbenzenemethanesulfonamide.

Workup

  1. filtrationThe mixture was filtered
  2. customthe ethanol removed in vacuo
  3. additionThe resulting aqueous solution was treated with 15% aqueous potassium hydroxide
  4. customPrecipitate began forming at pH four
  5. customThe product was isolated by filtration
  6. customdried for sixteen hours at 65° C. at 0.05 mm Hg

Sources & evidence

ORD record
ord-a075d84c5e3a45d28ebb2f59d84a7081
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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