Hydrochloric Acid → 3-Methylsulfamoylbenzylamine hydrochloride

HRID 219676Notes

Reaction equation

HRID 219676 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[ClH:14].[H][H]>CO.O.[Pd]>[ClH:14].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 175619913-cyano-N-methylbenzene-1-sulfonamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 691225733-Methylsulfamoylbenzylamine hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-cyano-N-methyl-benzenesulfonamide (4.88 g, 2.49 mmol) in MeOH (160 mL) is added concentrated HCl in water (16 mL) followed by the addition of Palladium on Carbon (10 wt %, 50 wt % water, 1.6 g). With magnetic stirring, the reaction is alternately placed under vacuum and 1 atmosphere of hydrogen (balloon) for three cycles. The reaction is then left under 1 atmosphere of hydrogen with stirring for 2 days. The reaction is filtered through celite and fresh Palladium on Carbon (10 wt %, 50 wt % water, 1.6 g) is added. The reaction is stirred for 24 hours under 1 atmosphere of hydrogen. The reaction is filtered through celite and the filtrate is concentrated in vacuo to provide 3-aminomethyl-N-methyl-benzenesulfonamide hydrochloride, as a solid (99%). MS: 201 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 2.41 (d, 3H), 4.12 (d, 2H), 7.23-7.57 (m, 2H), 7.70 (d, 1H), 7.81 (d, 1H), 8.49 (broad-s, 3H).

Workup

  1. filtrationThe reaction is filtered through celite and fresh Palladium on Carbon (10 wt %, 50 wt % water, 1.6 g)
  2. additionis added
  3. stirringThe reaction is stirred for 24 hours under 1 atmosphere of hydrogen
  4. filtrationThe reaction is filtered through celite
  5. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-5b28255ffafd4a14adb938daa6ea6a97
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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