2-Cyanoethanethioamide → HCID 10065884, compound

HRID 855904Notes

Reaction equation

HRID 855904 reaction equation
Br[CH:2]1[C:8](=O)[C:7]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:6]=2[S:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.[C:19]([CH2:21][C:22]([NH2:24])=[S:23])#[N:20]>C(O)C>[Cl:14][C:12]1[CH:11]=[CH:10][C:7]2[C:8]3[N:24]=[C:22]([CH2:21][C:19]#[N:20])[S:23][C:2]=3[C:3]3[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=3[S:5][C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 14162772-CyanoethanethioamideHCID 69515577HCID 69515577, compound

Product 1

HCID 10065884HCID 10065884, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 11-bromo-7-chloro-11H-dibenzo[b,f]thiepin-10-one (3.75 mmoles) in absolute ethanol (19 ml), 2-cyanothioacetamide (5.63 mmoles) was added. The reaction mixture was heated under stirring and refluxing for 8 hours. Then the solvent was evaporated under reduced pressure and the remaining dry residue was dissolved in water and ethyl acetate. After extraction the organic layers were washed with a saturated aqueous NaHCO3 solution, water and a saturated aqueous sodium chloride solution. After purification by chromatography on a silica gel column a crystalline product was isolated.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxing for 8 hours
  3. customThen the solvent was evaporated under reduced pressure
  4. dissolutionthe remaining dry residue was dissolved in water
  5. extractionAfter extraction the organic layers
  6. washwere washed with a saturated aqueous NaHCO3 solution, water
  7. customAfter purification by chromatography on a silica gel column a crystalline product
  8. customwas isolated

Sources & evidence

ORD record
ord-88407d0f302b4459b6279f950ee36a4b
Source dataset
uspto-grants-2007_08
Patent number
US07262302B2

Reaction notes

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