Dimethyl Sulfate → 2-Bromopropionic acid N-cyano-N-methylamide

HRID 235547Notes

Reaction equation

HRID 235547 reaction equation
[N:1]#[C:2][NH2:3].[Br:4][CH:5]([CH3:9])[C:6](Br)=[O:7].[C:10](=O)(O)[O-].[Na+].COS(OC)(=O)=O>[OH-].[K+]>[C:2]([N:3]([CH3:10])[C:6](=[O:7])[CH:5]([Br:4])[CH3:9])#[N:1]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 9864CyanamideHCID 79047Propanoyl bromide, 2-bromo-HCID 516892Sodium Bicarbonate

Product 1

HCID 537447922-Bromopropionic acid N-cyano-N-methylamideYield 35.6%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

10.5 g (0.25 mole) of cyanamide are dissolved in 250 ml of 2N potassium hydroxide solution and the solution so obtained is cooled to +10° C. At this temperature 26.5 ml (0.25 mole) of 2-bromopropionyl bromide are added dropwise and the reaction mixture is stirred for one hour at the same temperature. Then 16.8 g (0.2 mole) of sodium bicarbonate are added. 63 g (0.5 mole) of dimethylsulfate are subsequently added dropwise at 20° C. and the reaction mixture is stirred for 4 hours and extracted with methylene chloride. The combined orgnaic phases are dried over sodium sulfate and concentrated by evaporation, affording as residue 27.5 g of crude product. Vacuum distillation of this crude products yields 13.6 g (28.5% of theory) of 2-bromopropionic acid N-cyano-N-methylamide with a boiling point of 45°-47° C. at 0.008 mbar.

Workup

  1. customthe solution so obtained
  2. temperatureis cooled to +10° C
  3. stirringthe reaction mixture is stirred for 4 hours
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined orgnaic phases are dried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customaffording as residue 27.5 g of crude product
  8. distillationVacuum distillation of this crude products

Sources & evidence

ORD record
ord-cd67056207324113854dcca61edf3fc8
Source dataset
uspto-grants-1987_02
Patent number
US04640703

Reaction notes

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