Ethanol → HCID 13922897, compound

HRID 979593Notes

Reaction equation

HRID 979593 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[S:10][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:12][C:8]=2[CH:7]=1)([OH:3])=[O:2].[CH2:19](O)[CH3:20]>S(=O)(=O)(O)O>[C:1]([CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[S:10][C:11]([S:13](=[O:15])(=[O:14])[NH2:16])=[CH:12][C:8]=2[CH:7]=1)([O:3][CH2:19][CH3:20])=[O:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 13922886HCID 13922886, compound

Product 1

HCID 13922897HCID 13922897, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 5-(carboxymethoxy)benzo[b]thiophene-2-sulfonamide (1.50 g, 0.0052 m) in ethanol (15 ml) and concentrated sulfuric acid (3 ml) was refluxed with stirring for 5 hours. Ethanol was evaporated under reduced pressure, the residue was treated with H2O (25 ml) and extracted with ethyl acetate (50 ml and 2×25 ml). The combined extracts were washed with H2O, saturated sodium bicarbonate solution (2×25 ml), and three times with H2O. After drying over Na2SO4, the solvent was evaporated under reduced pressure to afford 1.43 g (87%) of product. Recrystallization from nitromethane afforded 1.12 g of analytically pure product melting at 167.5-168° C.

Workup

  1. temperaturewas refluxed
  2. customEthanol was evaporated under reduced pressure
  3. additionthe residue was treated with H2O (25 ml)
  4. extractionextracted with ethyl acetate (50 ml and 2×25 ml)
  5. washThe combined extracts were washed with H2O, saturated sodium bicarbonate solution (2×25 ml), and three times with H2O
  6. dry with materialAfter drying over Na2SO4
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eb2f8842dad944699fbbf943c595c927
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

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