Dimethylformamide → HCID 13922877, compound

HRID 2232357Notes

Reaction equation

HRID 2232357 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:10][C:6]=2[CH:5]=1.C([O-])(=O)C.[Na+].CN(C=O)C>O>[CH:3]([C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:10][C:6]=2[CH:5]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 13922876HCID 13922876, compound

Product 1

HCID 13922877HCID 13922877, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.0 g (0.012 mol) of 5-(2-bromoethyl)-2-sulfamoylbenzo[b]thiophene, 2.0 g (0.024 mol) of sodium acetate and 40 ml of DMF was heated at 100° C. under nitrogen. After 15 hours the mixture was poured into water and the aqueous phase was extracted 3× with ethyl acetate. The extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel by elution with 20% (V/V) ethyl acetate-hexane to yield 2.9 g (30%) of 5-ethenyl-2-sulfamoylbenzo[b]thiophene, m.p. 168°-170° C. (1,2-dichloroethane). Further elution with 40% (V/V) ethyl acetate-hexane yielded 3.74 g (59%) of 5-(2-acetoxyethyl)-2-sulfamoylbenzo[b]thiophene, m.p. 120°-122° C. (1,2-dichloroethane).

Workup

  1. extractionthe aqueous phase was extracted 3× with ethyl acetate
  2. customThe extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was chromatographed on silica gel by elution with 20% (V/V) ethyl acetate-hexane

Sources & evidence

ORD record
ord-f0ad3dfdb1f946308aa0e4226dd36439
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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