Carbon Tetrachloride → Ethyl chlorocyanoacetate

HRID 2396579Notes

Reaction equation

HRID 2396579 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].[H][H].C(Cl)(Cl)(Cl)[Cl:14]>CS(C)=O>[Cl:14][CH:5]([C:3]#[N:4])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 554591Ethyl chlorocyanoacetateYield 82.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of NaH in 400 mL of DMSO at 20° C. were added dropwise 79.1 g of ethyl cyanoacetate (700 mmol). The solution was stirred for 1 h at 20° C. until no more hydrogen evolved from the reaction system. 156 mL (1.5 mol) of CCl4 were added carefully. Occasional cooling was applied so as to maintain the temperature between 20°-25° C. The mixture was carefully quenched with HOAc, extracted with CH2Cl2, dried over MgSO4, concentrated, and distilled to give 85.2 g of the title compound (82.5%).

Workup

  1. temperatureOccasional cooling
  2. temperatureto maintain the temperature between 20°-25° C
  3. customThe mixture was carefully quenched with HOAc
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-5aa6df918c2b4d7eaebff7ac4944fc44
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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