Hydrochloric Acid → 4'-(2-Amino-1-hydroxyethyl)methanesulfonanilide

HRID 1613650Notes

Reaction equation

HRID 1613650 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][C:10]([C:12]1[CH:22]=[CH:21][C:15]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:14][CH:13]=1)=[O:11])C1C=CC=CC=1.O.Cl.[H][H]>[Pd].CO>[NH2:8][CH2:9][CH:10]([C:12]1[CH:22]=[CH:21][C:15]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:14][CH:13]=1)[OH:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 54331090N-[4-(N,N-Dibenzylglycyl)phenyl]methanesulfonamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 222205904'-(2-Amino-1-hydroxyethyl)methanesulfonanilide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4'-(2-Dibenzylaminoacetyl)methanesulfonanilide (XXVI) (32.7 g) and Pd/C catalyst (1.5 g) were combined in MeOH (200 ml), H2O (25 ml), and concentrated HCl (6.6 ml) and shaken for 24 hours at 35° C. and 3 atmospheres pressure of hydrogen gas in a Parr hydrogenator, by which time three equivalents of hydrogen had been consumed. The catalyst was filtered off and the filtrate was evaporated to a white solid, which was recrystallized twice from 2-PrOH/H2O. This yielded 4.3 g of Compound (XXV).HCl, m.p. 178°-180°, whose elemental analysis for C, H, and N, NMR, and mass spectra were consistent with the indicated structure.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to a white solid, which
  3. customwas recrystallized twice from 2-PrOH/H2O

Sources & evidence

ORD record
ord-1c9cfea8426b42e0aa6e70a8c0548df3
Source dataset
uspto-grants-1993_03
Patent number
US05194450

Reaction notes

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