Potassium Cyanide → HCID 5302618, compound

HRID 341471Notes

Reaction equation

HRID 341471 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:15][CH3:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([NH2:17])[N:3]=1.[C-:18]#[N:19].[K+]>CS(C)=O.CCOC(C)=O>[NH2:17][C:4]1[N:5]=[C:6]([N:8]([CH2:15][CH3:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:7]=[C:2]([C:18]#[N:19])[N:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 80756180HCID 80756180, compound2×

Product 1

HCID 5302618HCID 5302618, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-N-ethyl-N-phenyl-[1,3,5]triazine-2,4-diamine (Intermediate 37, 400 mg, 1.60 mmol) was dissolved in anhydrous DMSO (5 mL) before the addition of potassium cyanide (200 mg, 3.07 mmol). The reaction mixture was stirred at 120 C in a pressure tube for 2 h before allowing to cool to room temperature. The product mixture was diluted with EtOAc (20 mL), extracted with water (2×10 mL), saturated sodium chloride (5 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The desired product was obtained and used directly without further purification (300 mg, 78%). Method C HPLC-MS: MH+ requires m/z=241. Found: m/z=241, Rt=1.27 min (89%).

Workup

  1. extractionextracted with water (2×10 mL), saturated sodium chloride (5 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-182eb276841647fe9f08b5def001413a
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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