Dimethylformamide → HCID 13922877, compound

HRID 979574Notes

Reaction equation

HRID 979574 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 3X 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 3X 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-e32cb8e60ba64506bb9f9eaa305c643a
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

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