Methyl iodide → HCID 4778817, compound

HRID 982012Notes

Reaction equation

HRID 982012 reaction equation
[OH-].[K+].[CH2:3]([C:6]#[N:7])[C:4]#[N:5].[CH3:8]I.Cl[CH2:11][C:12]#[N:13].[C:14](=[S:16])=[S:15]>O.CN(C)C=O>[CH3:8][S:15][C:14]1[S:16][C:11]([C:12]#[N:13])=[C:6]([NH2:7])[C:3]=1[C:4]#[N:5]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 7856ChloroacetonitrileHCID 8010MalononitrileHCID 14797Potassium Hydroxide

Product 1

HCID 4778817HCID 4778817, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A concentrated solution of 50 g of KOH in approximately 30 ml of water is slowly added dropwise to a solution of 26.5 g of malonic acid dinitrile in approximately 250 ml of dimethyl formamide to which 45 ml of carbon disulphide have been added. During the addition the mixture is stirred and kept at a temperature of 0°-10° C. by cooling. After 10 minutes, 60.0 g of methyl iodide are slowly added dropwise while stirring and cooling and then, after 30 minutes, 30.5 g of chloroacetonitrile. The cooling bath is removed and 4.0 g of powdered KOH are added, the temperature of the reaction mixture rising to approximately 42° C. After stirring for another hour at 30°-35°° C., 600 ml of water and 100 ml of diethyl ether are added, after which the formed precipitate is sucked off, washed successively with water, isopropyl alcohol and diethyl ether, and dried. The desired product is obtained in a yield of 54.5 g and sublimates at 260° C.

Workup

  1. additionhave been added
  2. additionDuring the addition the mixture
  3. customkept at a temperature of 0°-10° C.
  4. temperatureby cooling
  5. stirringwhile stirring
  6. temperaturecooling
  7. waitafter 30 minutes
  8. customThe cooling bath is removed
  9. addition4.0 g of powdered KOH are added
  10. customrising to approximately 42° C
  11. stirringAfter stirring for another hour at 30°-35°° C
  12. addition, 600 ml of water and 100 ml of diethyl ether are added
  13. washwashed successively with water, isopropyl alcohol and diethyl ether
  14. customdried

Sources & evidence

ORD record
ord-fe987b5f74864a2d895a13fabb08a32e
Source dataset
uspto-grants-1991_02
Patent number
US04994485

Reaction notes

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