Ammonia → HCID 12687106, compound

HRID 866910Notes

Reaction equation

HRID 866910 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 3.4g of 9-chloro-2-fluoro-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin, 2.1g of copper cyanide, 0.2g of anhydrous copper sulfate and 50ml of N-methyl pyrrolidone was heated at 200°-210° C overnight. After cooling, to the reaction mixture were added 10ml of conc. aqueous ammonia and 100ml 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 0.3g 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-42916eed74474040bdc7b1540b5b2cc6
Source dataset
uspto-grants-1978_07
Patent number
US04101667

Reaction notes

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