HCID 14476487, compound → HCID 14476489, compound

HRID 1904950Notes

Reaction equation

HRID 1904950 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](S(C1C=CC=CC=1)(=O)=O)[C:7]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:6]2>[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:6]2

Participants

3

Reactant 1

HCID 14476487HCID 14476487, compound

Product 1

HCID 14476489HCID 14476489, compoundYield 4,647.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

5-methoxy-1-benzenesulfonyl-2-sulfamoylindole (22.0 gm, 0.97 mmol) was dissolved in 10% sodium hydroxide (250 ml) and warmed to 90° C. for 1 hour. The cooled reaction mixture was extracted with ethyl acetate (2×150 ml) and neutralized with concentrated hydrochloric acid. The precipitate was collected via filtration and the filtrate was extracted with ethyl acetate (4×200 ml). The precipitate collected earlier was combined with the extracts and the extracts were washed with water (2×100 ml), brine (2×100 ml) and dried (MgSO4). The organic solvent was removed under vacuum to yield a brown solid 10.2 gm. The solid was recrystallized from water using decolorizing carbon to yield white crystals; 4.5 gm., m.p. 208°-209° C.

Workup

  1. customThe cooled reaction mixture
  2. extractionwas extracted with ethyl acetate (2×150 ml) and neutralized with concentrated hydrochloric acid
  3. filtrationThe precipitate was collected via filtration
  4. extractionthe filtrate was extracted with ethyl acetate (4×200 ml)
  5. customThe precipitate collected earlier
  6. washthe extracts were washed with water (2×100 ml), brine (2×100 ml)
  7. dry with materialdried (MgSO4)
  8. customThe organic solvent was removed under vacuum

Sources & evidence

ORD record
ord-075b65bcb9464b2d9b137a1133d34874
Source dataset
uspto-grants-1989_06
Patent number
US04840963

Reaction notes

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