Potassium Hydroxide → HCID 14097248, compound

HRID 568521Notes

Reaction equation

HRID 568521 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[N:8][NH2:9].[OH-].[K+]>C(OC(O)C)C.O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[C:3]3[S:4][CH:5]=[CH:6][C:2]=3[NH:9][N:8]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86160846HCID 86160846, compound

Product 1

HCID 14097248HCID 14097248, compoundYield 702.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 101298981-EthoxyethanolSolvent

Procedure

A solution of 1.0 g of (3-bromothien-2-yl) (4-methoxyphenyl)methanone hydrazone in 60 ml of ethoxyethanol was treated with an alkaline solution prepared by dissolving 6.0 g of 85% potassium hydroxide pellets in 20 ml of water. The resultant solution was stirred at 105°-110° for 30 minutes and to it under nitrogen was added 250 ml of finely powdered cuprous chloride. The darkened mixture was maintained at 105°-110° C. for an additional 90 minutes and quenched with water. The organic materials were extracted exhaustively with ethyl acetate/ether (1:1) and the combined organic solution was washed (four times) with water and dried. Evaporation of the solvents afforded a thick oil which was purified by passage through an alumina column. Elution with ether removed most of the dark impurities and further elution with 5% methanol/ether gave 5.2 g of an oil which solidified on scratching, m.p. 143°-144° C. For analysis, a small sample was recrystallized from ether/hexane without any change in the melting range.

Workup

  1. customprepared
  2. temperatureThe darkened mixture was maintained at 105°-110° C. for an additional 90 minutes
  3. customquenched with water
  4. extractionThe organic materials were extracted exhaustively with ethyl acetate/ether (1:1)
  5. washthe combined organic solution was washed (four times) with water
  6. customdried
  7. customEvaporation of the solvents
  8. customafforded a thick oil which
  9. customwas purified by passage through an alumina column
  10. washElution with ether
  11. customremoved most of the dark impurities and further elution with 5% methanol/ether

Sources & evidence

ORD record
ord-93602c0769994847bebf0a49afe65925
Source dataset
uspto-grants-1988_03
Patent number
US04728651

Reaction notes

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