Ethylene Glycol → HCID 20260898, compound

HRID 648055Notes

Reaction equation

HRID 648055 reaction equation
[Br:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([C:11](=O)[CH2:12][N:13]3[CH:17]=[CH:16][N:15]=[CH:14]3)[CH:9]=[CH:10][C:4]=2[C:3]=1[CH3:19].O.NN.C(O)CO.[OH-].[K+]>O>[Br:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([CH2:11][CH2:12][N:13]3[CH:17]=[CH:16][N:15]=[CH:14]3)[CH:9]=[CH:10][C:4]=2[C:3]=1[CH3:19]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20260911HCID 20260911, compound

Product 1

HCID 20260898HCID 20260898, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-bromo-6-(1-imidazolyl)acetyl-3-methylbenzo[b]thiophene (0.45 g.), 99% hydrazine hydrate (0.20 g.) and ethylene glycol (5.0 ml.) was heated on a steam bath for 2 hours and then cooled. Potassium hydroxide (0.24 g.) was added and the mixture was heated at 135° C. for 1.5 hours and then cooled and poured into water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with chloroform gave a small amount of impurity followed by pure product. Evaporation of the product-containing fractions gave 2-bromo-6-[2-(1-imidazolyl)ethyl]-3-methylbenzo[b]thiophene (0.40 g.) as a thick oil which was pure enough for further reaction.

Workup

  1. temperaturewas heated on a steam bath for 2 hours
  2. temperaturecooled
  3. temperaturecooled
  4. extractionThe mixture was extracted several times with ethyl acetate
  5. washthe combined extracts were washed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent
  8. customgave an oil which
  9. customwas chromatographed on silica gel
  10. washElution with chloroform
  11. customgave a small amount of impurity
  12. customEvaporation of the product-containing fractions

Sources & evidence

ORD record
ord-e6257c2f904441d9a3dd9dbccef89781
Source dataset
uspto-grants-1983_10
Patent number
US04410539

Reaction notes

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