Hydrochloric Acid → N-[4-(aminomethyl)-2,6-difluorophenyl]methanesulfonamide hydrochloride

HRID 1350851Notes

Reaction equation

HRID 1350851 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([F:9])[C:6]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:5]([F:15])[CH:4]=1)#[N:2].[ClH:16]>CO.O1CCCC1.[C].[Pd]>[ClH:16].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([F:15])[C:6]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:7]([F:9])[CH:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21097536N-(4-cyano-2,6-difluorophenyl)methanesulfonamide

Product 1

HCID 21097523N-[4-(aminomethyl)-2,6-difluorophenyl]methanesulfonamide hydrochlorideYield 80%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(4-cyano-2,6-difluorophenyl)methanesulfonamide (1.01 g, 4.35 mmol) in methanol (15 ml), tetrahydrofuran (15 ml) and 12 M aqueous solution of hydrogen chloride (5 ml) was hydrogenated over 10% palladium-carbon (250 mg) under ballon pressure for 3 h at ambient temperature. The catalyst was filtered through a pad of celite and the filter cake was washed with methanol. After the filtrate and washings were evaporated in vacuo, the residue was recrystallized from methanol and diisopropyl ether to give to furnish 953 mg (80% yield) of the title compound as a white solid.

Workup

  1. filtrationThe catalyst was filtered through a pad of celite
  2. washthe filter cake was washed with methanol
  3. customAfter the filtrate and washings were evaporated in vacuo
  4. customthe residue was recrystallized from methanol and diisopropyl ether
  5. customto give

Sources & evidence

ORD record
ord-38697a704d734ce28e1e5cc4764b35c7
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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