Hydrochloric Acid → Methanesulfonamide, N-(3-oxospiro(benzofuran-2(3H),1'-cyclopropan)-5-yl)-

HRID 894620Notes

Reaction equation

HRID 894620 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3.[CH3:14][S:15](Cl)(=[O:17])=[O:16].Cl>N1C=CC=CC=1>[CH3:14][S:15]([NH:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 12925991HCID 12925991, compound

Product 1

HCID 3055476Methanesulfonamide, N-(3-oxospiro(benzofuran-2(3H),1'-cyclopropan)-5-yl)-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-aminospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (0.519 g.) in pyridine (5 ml.) was added methanesulfonyl chloride (0.28 ml.) under ice-cooling, followed by stirring. The reaction mixture was poured into cooled dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to remove the solvent. The residue was recrystallized from ethanol. By the above procedure there was obtained 5-methylsulfonylaminospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one as colorless needles melting at 152°-154° C.

Workup

  1. temperaturecooling
  2. additionThe reaction mixture was poured
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customto remove the solvent
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-41791359b72e4a419fb5814ffd264535
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

Loading…