Chlorosuccinimide → HCID 13922903, compound

HRID 2232363Notes

Reaction equation

HRID 2232363 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([S:9](=[O:12])(=[O:11])[NH2:10])=[CH:8][C:4]=2[CH:3]=1.COC(OC)N(C)C.[Cl:23]N1C(=O)CCC1=O>CC#N>[Cl:23][C:3]1[C:4]2[CH:8]=[C:7]([S:9](=[O:11])(=[O:12])[NH2:10])[S:6][C:5]=2[CH:13]=[CH:14][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 31398Chlorosuccinimide2×HCID 78373Dimethylformamide dimethyl acetalHCID 13922842HCID 13922842, compound

Product 1

HCID 13922903HCID 13922903, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 5-hydroxy-2-sulfamoylbenzo[b]thiophene (3.0 g, 0.013 mole) in CH3CN (60 ml) was treated with N,N-dimethylformamide dimethylacetal (1.75 ml, 0.013 mole). Within 5 minutes, the protected sulfonamide started to precipitate. After 10 minutes, this was redissolved by the addition of CH3CN (65 ml). N-Chlorosuccinimide, (1.91 g, 0.0143 mole) was added in one portion and the mixture was stirred at ambient temperature. After 2 days, another 175 mg of N-chlorosuccinimide was added and stirring was continued for another 3 days. The solvent was evaporated under reduced pressure and the residual solid was triturated with H2O (100 ml) and collected. This solid then was suspended in 6N HCl (70 ml) and heated on the steam bath for 61/2 hours. The resulting solid was extracted into ethyl acetate. Evaporation of the washed and dried extract under reduced pressure left 3.1 g (90%) of 4-chloro-5-hydroxy-2-sulfamoylbenzo[ b]thiophene, m.p. 198°-201° C. Recrystallization from H2O, decolorizing with charcoal, gave 2.6 g, m.p. 203°-205° C.

Workup

  1. customto precipitate
  2. waitAfter 10 minutes
  3. dissolutionthis was redissolved by the addition of CH3CN (65 ml)
  4. waitAfter 2 days
  5. stirringstirring
  6. waitwas continued for another 3 days
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residual solid was triturated with H2O (100 ml)
  9. customcollected
  10. temperatureheated on the steam bath for 61/2 hours
  11. extractionThe resulting solid was extracted into ethyl acetate
  12. customEvaporation of the
  13. washwashed
  14. customdried
  15. extractionextract under reduced pressure
  16. waitleft 3.1 g (90%) of 4-chloro-5-hydroxy-2-sulfamoylbenzo[ b]thiophene, m.p. 198°-201° C
  17. customRecrystallization from H2O
  18. customgave 2.6 g, m.p. 203°-205° C.

Sources & evidence

ORD record
ord-ed3896ffa4e146a88ac96bf2616317eb
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

Loading…