Hydrochloric Acid → Phenylsulfamate

HRID 1613384Notes

Reaction equation

HRID 1613384 reaction equation
[Na].C(OC(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][S:18]([NH:21]C(OCC1C=CC=CC=1)=O)(=[O:20])=[O:19])C1C=CC=CC=1.Cl.[H][H]>CO.[Pd]>[C:12]1([O:17][S:18](=[O:19])(=[O:20])[NH2:21])[CH:11]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67854670HCID 67854670, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11030308PhenylsulfamateYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

The 2-(benzyloxycarbonylaminosulfonyloxy)benzoic acid benzyl ester sodium salt prepared above, [35.3 g (0.076 mole)] was suspended in 500 ml of methanol was mixed with 6.2 ml of concentrated hydrochloric acid and 2 g of 5% palladium on carbon wetted with 50 ml methanol. The mixture was hydrogenated with hydrogen gas for 4 hr and filtered. The filtrate was concentrated to an oil. The oil was suspended in THF and filtered to remove some solids. The clear filtrate was concentrated and mixed with 1,1,1-trichloroethanol to precipitate the product as 8.82 g of light purple solid obtained after filtration. The purple solid was dissolved in THF and the solution was treated with charcoal, filtered and concentrated. The solid was recrystallized from 1,1,1-trichloroethane to give 6.5 g of white solid (39%), mp 139°-140° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to an oil
  3. filtrationfiltered
  4. customto remove some solids
  5. concentrationThe clear filtrate was concentrated
  6. additionmixed with 1,1,1-trichloroethanol
  7. customto precipitate the product as 8.82 g of light purple solid
  8. customobtained
  9. filtrationafter filtration
  10. dissolutionThe purple solid was dissolved in THF
  11. additionthe solution was treated with charcoal
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe solid was recrystallized from 1,1,1-trichloroethane

Sources & evidence

ORD record
ord-f0d556d0f8c640efa256b0134aabdac7
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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