Ethanol → HCID 13490388, compound

HRID 485468Notes

Reaction equation

HRID 485468 reaction equation
C(C1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:18]=1)#N.[OH-:19].[Na+].[CH2:21]([OH:23])[CH3:22]>>[F:17][C:14]1[CH:15]=[CH:16][C:9]2[S:8][C:7]3[CH:18]=[C:22]([C:21]([OH:19])=[O:23])[CH:4]=[CH:5][C:6]=3[CH:12]=[CH:11][C:10]=2[CH:13]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 134903873-Cyano-8-fluorodibenzo[b,f]thiepine

Product 1

HCID 13490388HCID 13490388, compound

Procedure

Suspend 300 mg. of the cyano compound of Step 1 in 8 ml. of 20% aqueous sodium hydroxide and 8 ml. of absolute ethanol. Reflux under nitrogen for 2 hours. Evaporate the ethanol. Acidify the suspension with 20% hydrochloric acid and separate the solids by filtration. Dissolve the residue in 20 ml. of hot methanol and add a few drops of concentrated hydrochloric acid. Evaporate the methanol, dilute with ether and evaporate again. Dilute with water, stir for 30 minutes, and filter. Wash the solids with water and dry in vacuo at 100° C. to obtain the title product (m.p., 270°-272° C.).

Workup

  1. temperatureReflux under nitrogen for 2 hours
  2. customEvaporate the ethanol
  3. customseparate the solids
  4. filtrationby filtration
  5. dissolutionDissolve the residue in 20 ml
  6. additionof hot methanol and add a few drops of concentrated hydrochloric acid
  7. customEvaporate the methanol
  8. additiondilute with ether
  9. customevaporate again
  10. additionDilute with water
  11. filtrationfilter
  12. washWash the solids with water
  13. customdry in vacuo at 100° C.

Sources & evidence

ORD record
ord-68682442c730484fad02e543696ae126
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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