Ammonia → HCID 12687106, compound

HRID 903629Notes

Reaction equation

HRID 903629 reaction equation
Cl[C:2]1[C:7]2[CH2:8][C:9](=[O:18])[C:10]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cu](C#N)[C:20]#[N:21].CN1CCCC1=O.N>S([O-])([O-])(=O)=O.[Cu+2].O>[C:20]([C:2]1[C:7]2[CH2:8][C:9](=[O:18])[C:10]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:21]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 12687103HCID 12687103, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 12687106HCID 12687106, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Procedure

The mixture of 3.4 g of 9-chloro-2-fluoro-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin, 2.1 g of copper cyanide, 0.2 g of anhydrous copper sulfate and 50 ml of N-methyl pyrrolidone was heated at 200°-210° C. overnight. After cooling, to the reaction mixture were added 10 ml of conc. aqueous ammonia and 100 ml of water and the resulting mixture was extracted with benzene. The benzene layer thus obtained was washed with water, dried over anhydrous sodium sulfate and the solvent was distilled off. The resulting residue was chromatographed over silica gel, and eluted with chloroform and benzene. There was obtained from benzene eluate 0.3 g of 9-cyano-2-fluoro-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin as yellow needles having a melting point of 174°-175° C.

Workup

  1. temperaturewas heated at 200°-210° C. overnight
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionthe resulting mixture was extracted with benzene
  4. customThe benzene layer thus obtained
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe resulting residue was chromatographed over silica gel
  9. washeluted with chloroform and benzene

Sources & evidence

ORD record
ord-d68f5795bc8940ba9018ad2a7f7b6908
Source dataset
uspto-grants-1980_10
Patent number
US04228284

Reaction notes

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