Ethyl bromoacetate → HCID 13922855, compound

HRID 2232343Notes

Reaction equation

HRID 2232343 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[C:15]([S:17](=[O:20])(=[O:19])[NH2:18])[S:14][C:13]=2[CH:21]=1.C(=O)(O)[O-].[K+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH2:6]([O:5][C:3]([CH2:2][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[C:15]([S:17](=[O:19])(=[O:20])[NH2:18])[S:14][C:13]=2[CH:21]=1)=[O:4])[CH3:7]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 146921L 650719HCID 516893Potassium Bicarbonate

Product 1

HCID 13922855HCID 13922855, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a solution of ethyl bromoacetate (1.2 ml, 11 mmol) and 6-hydroxy-2-sulfamoylbenzo[b]thiophene (2.29 g, 10 mmol) in DMSO (10 ml) was added dropwise a solution of potassium bicarbonate (1.0 g, 10 mmol) and potassium carbonate (0.13 g, 1 mmol) in water (7 ml). The mixture was stirred for 1-2 days, then diluted with water. The precipitated product was collected dissolved in ethyl acetate, dried (Na2SO4) and evaporated to dryness. The residue was recrystallized from hot ethyl acetate, boiling off solvent until crystallization began, to give 1.2 g of product, m.p. 182°-184° C.

Workup

  1. customThe precipitated product was collected
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customThe residue was recrystallized from hot ethyl acetate
  6. customuntil crystallization

Sources & evidence

ORD record
ord-98d9c8995cb249779d2735aba4775672
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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