Potassium Hydroxide → HCID 54216041, compound

HRID 26371Notes

Reaction equation

HRID 26371 reaction equation
[OH:1][CH:2]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]([NH:12]C(=O)C)[CH2:5][CH2:4][CH2:3]1.[OH-].[K+]>O.C(O)CO.O>[OH:1][C@H:2]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[C@H:6]([NH2:12])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21322967HCID 21322967, compound

Product 1

HCID 54216041HCID 54216041, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 20437942Ethylene glycol waterSolvent

Procedure

A sample of a cis/trans mixture of N-(5,6,7,8-tetrahydro-8-hydroxy-4H-cyclohepta[b]thien-4-yl)acetamide is added to 2 equivalents of KOH in water/ethylene glycol mixture. The mixture is heated at reflux under nitrogen atmosphere until starting material is no longer detectable by thin-layer chromatography. The mixture is cooled, diluted with water and extracted exhaustively with CHCl3. The chloroform extract is added to an equal volume of water and acidified with hydrochloric acid until the mixture is at pH 2. The mixture is then extracted with CHCl3 and then the remaining aqueous solution is made alkaline with NaOH solution. The alkaline solution is then extracted with CHCl3 exhaustively and the extracts are dried over MgSO4 and evaporated to dryness to afford the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux under nitrogen atmosphere
  3. temperatureThe mixture is cooled
  4. extractionextracted exhaustively with CHCl3
  5. extractionThe chloroform extract
  6. additionis added to an equal volume of water
  7. extractionThe mixture is then extracted with CHCl3
  8. extractionThe alkaline solution is then extracted with CHCl3 exhaustively
  9. dry with materialthe extracts are dried over MgSO4
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-44c1d12cad124dfe831f55ae90946c40
Source dataset
uspto-grants-1979_04
Patent number
US04150035

Reaction notes

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