Calcium Chloride → HCID 23337044, compound

HRID 903651Notes

Reaction equation

HRID 903651 reaction equation
Cl[C:2]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH3:19])[CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cu](C#N)[C:21]#[N:22].[Cl-].[Ca+2].[Cl-].O.N>S([O-])([O-])(=O)=O.[Cu+2].O.CN1CCCC1=O>[C:21]([C:2]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH3:19])[CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:22]

Participants

8

Reactant 4

HCID 5284359Calcium ChlorideHCID 12896473Azane;hydrateHCID 23337057HCID 23337057, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 23337044HCID 23337044, compoundYield 29.8%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The mixture of 520 mg of 9-chloro-10,11-dihydro-2-ethoxydibenzo-[b,f]thiepin, 0.1 g of copper sulfate, 1 g of copper cyanide and 20 ml of N-methylpyrrolidone was refluxed with stirring for 15 hrs., while preventing the moisture with calcium chloride. After cooling, to this was added 20 ml of conc. ammonia water and 100 ml of water, and the mixture was extracted. The extract was washed with water, dried over anhydrous potassium carbonate and, the solvent was evaporated to obtain the residue. This was chromatographed on silica gel, eluted with the mixed solvent of benzene and n-hexane(4:1) and there was obtained 150 mg of 9-cyano-10,11-dihydro-2-ethoxydibenzo[b,f]thiepin having a melting point of 124° to 126° C. as colorless powdered crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous potassium carbonate
  6. customthe solvent was evaporated
  7. customto obtain the residue
  8. customThis was chromatographed on silica gel
  9. washeluted with the mixed solvent of benzene and n-hexane(4:1)

Sources & evidence

ORD record
ord-2f5f739c175c41b68374ace887d48431
Source dataset
uspto-grants-1980_10
Patent number
US04228284

Reaction notes

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