Methane → 2-(Sulfamoyloxy)benzoic acid

HRID 1493976Notes

Reaction equation

HRID 1493976 reaction equation
[Na].C1(C[O:9][C:10](=[O:29])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][S:18]([NH:21]CC2C=CC=CC=2)(=[O:20])=[O:19])C=CC=CC=1.Cl.C>CO.[Pd].C1COCC1>[NH2:21][S:18]([O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]([OH:29])=[O:9])(=[O:20])=[O:19]

Participants

7

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 86744858HCID 86744858, compound

Product 1

HCID 149150902-(Sulfamoyloxy)benzoic acidYield 39.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-[[(phenylmethyl)aminosulfonyl]oxy]benzoic acid (phenylmethyl)ester sodium salt (35.3 g, 0.076 mole) in methanol (500 ml) was added 6.2 ml of concentrated hydrochloric acid and 2 g of 5% palladium on carbon catalyst wetted with methanol (50 ml). The mixture was hydrogenated for 4 hr and filtered. The filtrate was concentrated to an oil and resuspended in THF. The solids were removed by filtration and the filtrate concentrated. The residue was triturated with 1,1,1-trichloroethane, giving 8.82 g of light purple solid. The solid was dissolved in THF, treated with activated charcoal, filtered, and concentrated again. The residue was recrystallized from 1,1,1-trichloroethane to give 6.5 g of white solid, mp 139°-140° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to an oil
  3. customThe solids were removed by filtration
  4. concentrationthe filtrate concentrated
  5. customThe residue was triturated with 1,1,1-trichloroethane
  6. customgiving 8.82 g of light purple solid
  7. filtrationfiltered
  8. concentrationconcentrated again
  9. customThe residue was recrystallized from 1,1,1-trichloroethane

Sources & evidence

ORD record
ord-ceead67bf5584adcb64068f9c8bbcda8
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

Loading…