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Hydrazine hydrate (1:1) → 9-Cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin hydrazone

HRID 866915
Notes
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Reaction equation

HRID 866915 reaction equation
[C:1]([C:3]1[C:8]2[CH2:9][C:10](=O)[C:11]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2].O.[NH2:22][NH2:23]>C(O)C.O1CCOCC1>[C:1]([C:3]1[C:8]2[CH2:9][C:10](=[N:22][NH2:23])[C:11]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 126871079-Cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin

Product 1

HCID 867358609-Cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin hydrazoneYield 79.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

900mg of 9-cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo-[b,f]thiepin was dissolved in the mixed solvent of 8ml of ethanol and 8ml of dioxane. To this was added 1.0g of 100% hydrazine hydrate and the resulting mixture was refluxed with stirring for 7.5 hours. After the completion of reaction, the solvent was distilled off to obtain the residue, which was washed with a small amount of ethanol, and there was obtained 750mg of 9-cyano-2-methoxy-10,11-dihydro-11-oxo-dibenzo[b,f]thiepin hydrazone as colorless needles having a melting point of 186°-187° C.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. customAfter the completion of reaction
  3. distillationthe solvent was distilled off
  4. customto obtain the residue, which
  5. washwas washed with a small amount of ethanol

Sources & evidence

ORD record
ord-3761bb5d5ac64d35a86bc4e7edf3dde1
Source dataset
uspto-grants-1978_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04101667

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes