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

HRID 1029742Notes

Reaction equation

HRID 1029742 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-75bb528ef9ba482fa9f2c922dfb3f33b
Source dataset
uspto-grants-1992_04
Patent number
US05102914

Reaction notes

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