Chloroacetyl chloride → N'-(2-chloroacetyl)-2,2-dimethylpropanehydrazide

HRID 2261308

Reaction equation

HRID 2261308 reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[C:3]([NH:5][NH2:6])=[O:4].[Cl:9][CH2:10][C:11](Cl)=[O:12].C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:9][CH2:10][C:11]([NH:6][NH:5][C:3](=[O:4])[C:2]([CH3:8])([CH3:7])[CH3:1])=[O:12]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 5451472,2-Dimethylpropanehydrazide

Product 1

HCID 54595759N'-(2-chloroacetyl)-2,2-dimethylpropanehydrazideYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 2.86 g of 2,2-dimethylpropanohydrazide was dissolved in tetrahydrofuran, and 2.78 g of chloroacetyl chloride was then added at 0° C. The mixture was stirred at room temperature for 18 hours. After aqueous saturated sodium hydrogen carbonate was added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 2.58 g of N′-(chloroacetyl)-2,2-dimethylpropanohydrazide.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5cf7205564d4fd7923659e905550472
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Linked notes

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