Potassium Hydroxide → HCID 21293966, compound

HRID 622214Notes

Reaction equation

HRID 622214 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])=[N:8][NH2:9].C(OC(O)C)C.[OH-].[K+]>O.ClCCl.Cl[Cu]>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:7]1[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[NH:9][N:8]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 101298981-EthoxyethanolHCID 86160838HCID 86160838, compound

Product 1

HCID 21293966HCID 21293966, compoundYield 53.5%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.23 g of (3-bromthien-2-yl) (2-methoxyphenyl)methanone hydrazone and 47 ml of ethoxyethanol was heated at 75° C. and to it a solution of potassium hydroxide in water (1.88 g in 9.15 ml) was added. The reaction mixture was blanketed with nitrogen. After stirring for 10 minutes, 50 mg of CuCl was then added and stirring was continued until completion of the reaction (45 minutes). The reaction mixture was then allowed to cool to room temperature, quenched with water and the organics were extracted into ether/ethyl acetate (1:1). Washing, drying (over anhydrous magnesium sulfate) and then evaporation of the ether/ethyl acetate solution gave an oil containing some crystals. The oil was passed through a silica gel column packed in dichloromethane to give 2.07 g of crystals. This material was combined with another material prepared in the same manner. The combined product (3.1 g) was recrystallized from ether/hexane.

Workup

  1. additionwas added
  2. stirringstirring
  3. customwas continued until completion of the reaction (45 minutes)
  4. customquenched with water
  5. extractionthe organics were extracted into ether/ethyl acetate (1:1)
  6. washWashing
  7. dry with materialdrying (over anhydrous magnesium sulfate)
  8. customevaporation of the ether/ethyl acetate solution
  9. customgave an oil
  10. additioncontaining some crystals

Sources & evidence

ORD record
ord-0399048c7e5242df98a8d3844249bdee
Source dataset
uspto-grants-1988_09
Patent number
US04769472

Reaction notes

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