Sodium Cyanide → HCID 22907086, compound

HRID 742038Notes

Reaction equation

HRID 742038 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[C-:8]#[N:9].[Na+].[Cl-:11].[NH4+:12].C(=O)([O-])[O-].[K+].[K+]>CO.O>[ClH:11].[NH2:12][C:4]1([C:8]#[N:9])[CH2:5][CH2:6][S:1][CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 66173Tetrahydrothiopyran-4-one

Product 1

HCID 22907086HCID 22907086, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of tetrahydrothiopyran-4-one (4.64 g, 40.0 mmol) in methanol (10 mL) is added to a mixture of sodium cyanide (2.0 g, 40.0 mmol) and ammonium chloride (2.36 g, 44.0 mmol) in water (8 mL). The reaction mixture is heated to reflux for 14 hours. The mixture is diluted with water, basified with potassium carbonate, and extracted with diethyl ether. The organic extract is dried (MgSO4) and filtered. The solution is acidified with hydrochloric acid saturated with methylene chloride. The resulting precipitate is filtered off providing 4-amino-4-cyano-tetrahydrothiopyran hydrochloride salt.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 14 hours
  3. extractionextracted with diethyl ether
  4. extractionThe organic extract
  5. dry with materialis dried (MgSO4)
  6. filtrationfiltered
  7. filtrationThe resulting precipitate is filtered off

Sources & evidence

ORD record
ord-97dc5b924a914ba985ae5b55c0017de1
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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