Potassium Iodide → Cyanomethyl 2-(cyanomethylthio)nicotinate

HRID 27233Notes

Reaction equation

HRID 27233 reaction equation
Cl[CH2:2][C:3]#[N:4].[SH:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[C:15](=O)(O)[O-].[K+].[I-].[K+].[Cl-].[Na+].C[N:25]([CH3:28])C=O>O>[C:3]([CH2:2][S:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([O:10][CH2:15][C:28]#[N:25])=[O:9])#[N:4]

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 516893Potassium BicarbonateHCID 178524460HCID 178524460, compound

Product 1

HCID 2532264Cyanomethyl 2-(cyanomethylthio)nicotinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12 Grams (0.16 mole) of chloroacetonitrile was added to a stirred suspension of 6.2 g (0.04 mole) of 2-mercaptonicotinic acid, 8.0 g (0.08 mole) of potassium bicarbonate, and 20 g (0.12 mole) of potassium iodide in 100 ml of dimethylformamide at 10° under nitrogen. The reaction was stirred at 10° for 7 hr., then at 25° for 15 hr. The reaction mixture was then poured into water, saturated with sodium chloride and filtered. The resulting solid was dissolved in methylene chloride, dried with magnesium sulfate and evaporated to give 7.5 g of cyanomethyl 2-(cyanomethylthio)nicotinate. m.p. 140°-143° C. NMR (DMSO) δ3.3(s,2); 4.3(s,2); 6.4(dd,1); 7.4(dd,1); 7.8(dd,1).

Workup

  1. wait, then at 25° for 15 hr
  2. filtrationfiltered
  3. dissolutionThe resulting solid was dissolved in methylene chloride
  4. dry with materialdried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-db111377924643b9a7c91b19da1e9bd3
Source dataset
uspto-grants-1980_09
Patent number
US04220776

Reaction notes

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