Dimethyl Sulfoxide → HCID 10487636, compound

HRID 372028Notes

Reaction equation

HRID 372028 reaction equation
CS(C)=O.[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.Cl.[CH3:15][NH2:16].[C-:17]#[N:18].[Na+]>O>[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]([NH:18][CH3:17])[C:15]#[N:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 69962-ChlorobenzaldehydeHCID 8929Sodium CyanideHCID 6364545Methylamine hydrochloride

Product 1

HCID 10487636HCID 10487636, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture containing 50 milliliters (ml) of dimethylsulfoxide, 15 ml of water, 29 grams (g) of 2-chlorobenzaldehyde, 15 g of methylaminehydrochloride and 12.5 g of sodium cyanide is stirred at room temperature for approximately 76 hours. The reaction mixture is then diluted with water and extracted with benzene. The benzene extract is washed several times with water and then dried over potassium carbonate. Filtration and evaporation of the filtrate under reduced pressure yields crude 2-(2-chlorophenyl)-2-methylaminoacetonitrile. This material is dissolved in approximately 100 ml of ether and added to a solution of 13 g of lithium aluminum hydride in 300 ml of ether. The reaction temperature is kept between -10° and 5° C at first and is then allowed to warm to room temperature. After stirring for about 20 hours there is added cautiously and dropwise first 13 ml of water, then 13 ml of 15% sodium hydroxide and finally 20 ml of water. The mixture is stirred until the solid is nearly white and the solid is then removed by filtration.

Workup

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. washis washed several times with water
  4. dry with materialdried over potassium carbonate
  5. filtrationFiltration and evaporation of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-de5feab0d2f443429c810c88307e8477
Source dataset
uspto-grants-1978_05
Patent number
US04088771

Reaction notes

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