Sodium Cyanide → HCID 12852741, compound

HRID 1105884Notes

Reaction equation

HRID 1105884 reaction equation
Cl[C:2]1[S:6][N:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[CH:3]=1.[C-:16]#[N:17].[Na+]>C(Cl)(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:16]([C:2]1[S:6][N:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[CH:3]=1)#[N:17]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 13013787HCID 13013787, compound

Product 1

HCID 12852741HCID 12852741, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4.8 g. (0.02 mole) of 5-chloro-2-phenethyl-4-isothiazolin-3-one in 25 ml of CHCl3, 1.0 g. (0.02 mole) of sodium cyanide in 5 ml of water and 0.015 g of tetrabutyl ammonium bromide was heated under reflux for 1 hour, while stirring. The mixture was then washed with water, dried, and concentrated to give a gummy brown residue, which was recrystallized from 300 ml of ethanol to give 0.15 g. of the named product, mp 228°-230 (softened at 210°).

Workup

  1. additionA mixture of 4.8 g
  2. temperatureunder reflux for 1 hour
  3. washThe mixture was then washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto give a gummy brown residue, which
  7. customwas recrystallized from 300 ml of ethanol
  8. customto give 0.15 g
  9. custom230 (softened at 210°)

Sources & evidence

ORD record
ord-15c025393f174b258986b72caac078b0
Source dataset
uspto-grants-1982_01
Patent number
US04310590

Reaction notes

Loading…