HCID 54154263, compound → Sulfamic acid 2-(3-hydroxyphenoxy)ethyl ester

HRID 327747Notes

Reaction equation

HRID 327747 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=2)[O:12][CH2:13][CH2:14][O:15][S:16](=[O:19])(=[O:18])[NH2:17])C=CC=CC=1>O1CCCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[O:12][CH2:13][CH2:14][O:15][S:16](=[O:18])(=[O:19])[NH2:17]

Participants

4

Reactant 1

HCID 54154263HCID 54154263, compound

Product 1

HCID 54256968Sulfamic acid 2-(3-hydroxyphenoxy)ethyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 17.1 g (0.053 mole) of sulfamic acid 2-[3-(phenylmethoxy)phenoxy]ethyl ester in 250 ml of tetrahydrofuran was added 0.5 teaspoon of 5% palladium on carbon catalyst and the mixture was hydrogenated in a Parr bottle at 40° C. for 2 hr. The catalyst was removed and a fresh 0.5 teaspoon of 5% palladium on carbon catalyst was added and the mixture was hydrogenated at 40° C. for 19 hr, whereby hydrogen uptake ceased. The catalyst was removed by filtration through Celite® and the solvent was evaporated under reduced pressure to yield 12.3 g of a brown, viscous oil that solidified after standing for five weeks at ambient temperature. The solid was triturated with ethyl ether-petroleum ether into a paste. The solvents were decanted and the paste was dried to yield 8.9 g (72%) a white solid, mp 56°-60° C.

Workup

  1. customThe catalyst was removed
  2. additiona fresh 0.5 teaspoon of 5% palladium on carbon catalyst was added
  3. waitthe mixture was hydrogenated at 40° C. for 19 hr
  4. customThe catalyst was removed by filtration through Celite®
  5. customthe solvent was evaporated under reduced pressure
  6. customto yield 12.3 g of a brown, viscous oil that solidified
  7. waitafter standing for five weeks at ambient temperature
  8. customThe solid was triturated with ethyl ether-petroleum ether into a paste
  9. customThe solvents were decanted
  10. customthe paste was dried

Sources & evidence

ORD record
ord-a321304dc1e444779a379626d631f85d
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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