Hydrochloric Acid → HCID 18543276, compound

HRID 1268043Notes

Reaction equation

HRID 1268043 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][C:11]#[N:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.O.Cl.[OH-].[Na+]>COCCOC>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][CH2:10][CH2:11][NH2:12])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 185430192-[(3,5-Dichlorophenyl)thio]acetonitrile

Product 1

HCID 18543276HCID 18543276, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of (3,5-dichlorophenylthio)acetonitrile (1.2g), in 3.0 mL of ethylene glycol dimethyl ether is added 0.61 mL of 10M borane dimethyl sulfide complex and the mixture heated at reflux for 0.5 hours. The reaction is cooled in an ice bath and 2.0 mL of water and 2.0 mL of concentrated hydrochloric acid is added. This mixture is heated at reflux for 0.5 hr. The clear solution is then cooled and basified with 5N sodium hydroxide and extracted with ether. The ether extract is dried over potassium carbonate, filtered and concentrated to give 1.0 g of a colorless oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 0.5 hours
  3. temperatureThe reaction is cooled in an ice bath
  4. temperatureThis mixture is heated
  5. temperatureat reflux for 0.5 hr
  6. temperatureThe clear solution is then cooled
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. dry with materialis dried over potassium carbonate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-76cf9ca4a3c04c3da256eaef39c687e4
Source dataset
uspto-grants-2003_04
Patent number
US06555561B2

Reaction notes

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