Hydrochloric Acid → 4-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide

HRID 42340Notes

Reaction equation

HRID 42340 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>Cl.CCO.[Pd]>[NH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([S:6]([NH:5][C:1]([CH3:3])([CH3:2])[CH3:4])(=[O:8])=[O:7])=[CH:10][C:11]=1[CH3:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58275375HCID 58275375, compound

Product 1

HCID 582753444-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamideYield 113.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21887872Ethanol hydrochlorideSolvent

Procedure

The reaction mixture of N-tert-butyl-4-cyano-3-methylbenzenesulfonamide (0.7176 g) and Pd/C (0.97 g) in 1N HCl/EtOH (1.5 ml 1N HCl in 15 ml EtOH) was stirred under H2 for 2 hours. Then 1N HCl (3 ml) was added to improve the reaction progress and it was stirred overnight. The reaction mixture was filtered through a pad of diatomaceous earth, washed with MeOH and concentrated to about 3 ml. The residue was diluted with H2O and lyophilized to give 0.8275 g 4-(aminomethyl)-N-tert-butyl-3-methylbenzenesulfonamide as white powder.

Workup

  1. stirringwas stirred overnight
  2. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  3. washwashed with MeOH
  4. concentrationconcentrated to about 3 ml
  5. additionThe residue was diluted with H2O

Sources & evidence

ORD record
ord-adae39ad027e4d13915efa2be87b76d5
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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