Sodium Cyanide → HCID 20096443, compound

HRID 1769963Notes

Reaction equation

HRID 1769963 reaction equation
Cl[CH2:2][C:3]1[C:11]2[S:10][N:9]=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[C-:12]#[N:13].[Na+]>C(Cl)(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:12]([CH2:2][C:3]1[C:11]2[S:10][N:9]=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:13]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 20096447HCID 20096447, compound

Product 1

HCID 20096443HCID 20096443, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

18.4 g of 7-chloromethylbenzo-1,2,3-thiadiazole are dissolved in 50 ml of chloroform, 0.5 g of tetrabutylammonium iodide are added, the mixture is heated to 50°-55° C. and treated dropwise in the course of 0.5 hours with a solution of 5.6 g of sodium cyanide in 20 ml of water, with stirring. Heating is continued overnight at the same temperature, on the following day the mixture is cooled, treated with water and extracted several times using dichloromethane. The extracts are washed with water, dried over sodium sulfate and filtered over Hyflo, and the filtrate is evaporated. The residue is purified on silica gel (hexane/ethyl acetate) resulting in the title compound of m.p. 78°-80° C.

Workup

  1. temperaturethe mixture is heated to 50°-55° C.
  2. temperatureHeating
  3. temperaturethe mixture is cooled
  4. extractionextracted several times
  5. washThe extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered over Hyflo
  8. customthe filtrate is evaporated
  9. customThe residue is purified on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2a114861143b4a9eba5a423b1df3599b
Source dataset
uspto-grants-1995_01
Patent number
US05384321

Reaction notes

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