Sodium Hydroxide → ((Dimethylamino)methylene)propanedinitrile

HRID 1658887Notes

Reaction equation

HRID 1658887 reaction equation
[C:1]([C:3](=[CH:6][N:7]([CH3:9])[CH3:8])[CH:4]=O)#[N:2].[NH2:10]OS(O)(=O)=O.[OH-].[Na+]>O>[CH3:8][N:7]([CH:6]=[C:3]([C:4]#[N:10])[C:1]#[N:2])[CH3:9]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 76284hydroxylamine-O-sulfonic acidHCID 2784272-Cyano-3-dimethylaminoacrolein

Product 1

HCID 28111((Dimethylamino)methylene)propanedinitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a slurry of 12.4 g. of 2-cyano-3-dimethylaminoacrolein in 50 ml. of water was added in small portions 13.6 g. of hydroxylamine-O-sulfonic acid (91% pure). The resulting clear solution was stirred for an additional 10 minutes, then cooled to 0° and adjusted to pH 6.0 by addition of approximately 26 ml. of 5N sodium hydroxide solution. The mixture was heated for 20 minutes in a water bath at 70°. A pH 3 was maintained over this period by dropwise addition of 5N sodium hydroxide solution. After cooling to room temperature, the mixture was extracted with 3 × 100 ml. of methylene chloride. The combined extracts were washed with 50 ml. of water, dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. Thus, dimethylaminomethylenemalononitrile was obtained. After recrystallization from isopropanol, the material had a melting point of 93°-95°.

Workup

  1. temperaturecooled to 0°
  2. additionadjusted to pH 6.0 by addition of approximately 26 ml
  3. temperatureThe mixture was heated for 20 minutes in a water bath at 70°
  4. extractionthe mixture was extracted with 3 × 100 ml
  5. washThe combined extracts were washed with 50 ml
  6. dry with materialof water, dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e61f7d2bf10947c089bbf9f97c689266
Source dataset
uspto-grants-1976_06
Patent number
US03966791

Reaction notes

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