HCID 54368629, compound → HCID 53940000, compound

HRID 327746Notes

Reaction equation

HRID 327746 reaction equation
C1(C[O:8][C:9]2[CH:22]=[CH:21][C:12]([O:13][CH2:14][CH2:15][O:16][S:17](=[O:20])(=[O:19])[NH2:18])=[CH:11][CH:10]=2)C=CC=CC=1>O1CCCC1.[Pd]>[OH:8][C:9]1[CH:22]=[CH:21][C:12]([O:13][CH2:14][CH2:15][O:16][S:17](=[O:19])(=[O:20])[NH2:18])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 54368629HCID 54368629, compound

Product 1

HCID 53940000HCID 53940000, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 25.8 g (0.08 mole) of sulfamic acid 2-[4-(phenylmethoxy)phenoxy]ethyl ester in 150 ml of tetrahydrofuran was added 0.5 teaspoon of 10% palladium on carbon catalyst and the mixture was hydrogenated in a Parr bottle at 40° C. overnight. The catalyst was removed and a fresh 0.5 teaspoon of 10% palladium on carbon catalyst was added and the mixture was hydrogenated at 40° C. for 3 hr whereby hydrogen uptake ceased. The catalyst was removed by filtration through Celite® and the filtrate was evaporated under reduced pressure to give a viscous oil that solidified upon standing. The solid was recrystallized from ethyl acetate-chloroform to yield 18.0 g (97%) of a shiny, white solid, mp 92°-93° C.

Workup

  1. customThe catalyst was removed
  2. additiona fresh 0.5 teaspoon of 10% palladium on carbon catalyst was added
  3. waitthe mixture was hydrogenated at 40° C. for 3 hr
  4. customThe catalyst was removed by filtration through Celite®
  5. customthe filtrate was evaporated under reduced pressure
  6. customto give a viscous oil that
  7. customThe solid was recrystallized from ethyl acetate-chloroform
  8. customto yield 18.0 g (97%) of a shiny, white solid, mp 92°-93° C.

Sources & evidence

ORD record
ord-edc91ba4f6b44ca58e665a70836e6e29
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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