Water → HCID 12687090, compound

HRID 866924Notes

Reaction equation

HRID 866924 reaction equation
[OH-:1].[Na+].[C:3]([C:5]1[C:10]2[CH2:11][C:12](=NN)[C:13]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:14]=3[S:15][C:9]=2[CH:8]=[CH:7][CH:6]=1)#N.[OH2:23]>C(O)COCCO>[C:3]([C:5]1[C:10]2[CH2:11][CH2:12][C:13]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:14]=3[S:15][C:9]=2[CH:8]=[CH:7][CH:6]=1)([OH:23])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 53670505HCID 53670505, compound

Product 1

HCID 12687090HCID 12687090, compound

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

To 1.0g of sodium hydroxide dissolved in 15ml of diethylene glycol was added 1.0g of 9-cyano-3-fluoro-10,11-dihydrodibenzo[b,f]thiepin-11-one hydrazone and the resulting mixture was heated with stirring at 190°-200° C for 2 hours. After cooling, water was added to the mixture, which was extracted with benzene. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain the residue, which was chromatographed over silica gel, and eluted with ethyl acetate-benzene (1:10), and there was obtained the crude product. Recrystallization from methanol afforded 102mg of 9-carboxy-3-fluoro-10,11-dihydrodibenzo[b,f]thiepin having a melting point of 209°-211° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureAfter cooling
  3. extractionwas extracted with benzene
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customto obtain the residue, which
  9. customwas chromatographed over silica gel
  10. washeluted with ethyl acetate-benzene (1:10)
  11. customthere was obtained the crude product
  12. customRecrystallization from methanol

Sources & evidence

ORD record
ord-3ff2dd525f934503937382b65fe3ece5
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

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