Sodium Acetate → HCID 13922872, compound

HRID 2232352Notes

Reaction equation

HRID 2232352 reaction equation
Br[CH2:2][C:3]1[CH:15]=[CH:14][C:6]2[S:7][C:8]([S:10](=[O:13])(=[O:12])[NH2:11])=[CH:9][C:5]=2[CH:4]=1.[C:16]([O-:19])(=[O:18])[CH3:17].[Na+]>C(N(CC)CC)C.C(O)(=O)C>[C:16]([O:19][CH2:2][C:3]1[CH:15]=[CH:14][C:6]2[S:7][C:8]([S:10](=[O:13])(=[O:12])[NH2:11])=[CH:9][C:5]=2[CH:4]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 13922868HCID 13922868, compound

Product 1

HCID 13922872HCID 13922872, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of 5-bromomethyl-2-sulfamoylbenzo[b]thiophene (3.06, 0.01 mol), anhydrous sodium acetate (0.98 g, 0.01 mol) and glacial acetic acid (15 ml) was added three drops of triethylamine. The mixture was heated and the resulting solution was stirred at reflux for 6 hours and was left at room temperature over night. The acetic acid was removed in vacuo and the residual gum was diluted with 25 ml of ice water. The product was extracted into 3×50 ml of ether. The combined extracts were washed with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 2.5 g of yellow solid (88% yield). Recrystallization from chloroform gave material with a m.p. 113°-115° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hours
  3. waitwas left at room temperature over night
  4. customThe acetic acid was removed in vacuo
  5. additionthe residual gum was diluted with 25 ml of ice water
  6. extractionThe product was extracted into 3×50 ml of ether
  7. washThe combined extracts were washed with water
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4db3ed2401cf47eb93bd54126fde44cd
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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