Dimethyl Sulfoxide → HCID 70606727, compound

HRID 972088Notes

Reaction equation

HRID 972088 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[C:4](C)=[CH:5][C:6](O)=[CH:7][CH:8]=1.ClC[C:14]#[N:15].[CH3:16]S(C)=O.[C:20]([O-:23])([O-])=O.[K+].[K+]>O>[CH3:11][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([CH3:16])=[CH:5][C:4]=1[O:23][CH2:20][C:14]#[N:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 84222Aminocarb phenol

Product 1

HCID 70606727HCID 70606727, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30.2 Grams of 4-dimethylamino-m-cresol and 16.0 grams of chloroacetonitrile were dissolved in 50 ml. of dimethylsulfoxide. Anhydrous K2CO3 (39.6 g) was added as a catalyst. The mixture was heated with stirring to 70°-80° C. for three hours. The reaction mixture was poured into approximately 2 liters of a ice and water mixture. The product was extracted with methylene chloride. The extract was dried with SEA SORB® and activated charcoal and the resulting mixture was filtered. The filtrate was dried under vacuum to yield 4-dimethylamino-m-tolyloxyacetonitrile.

Workup

  1. temperatureThe mixture was heated
  2. extractionThe product was extracted with methylene chloride
  3. dry with materialThe extract was dried with SEA SORB® and activated charcoal
  4. filtrationthe resulting mixture was filtered
  5. customThe filtrate was dried under vacuum

Sources & evidence

ORD record
ord-08cdd671e4394d8baa938d5b9f1ae3b5
Source dataset
uspto-grants-1979_07
Patent number
US04163105

Reaction notes

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