Phosgene → Ethyl 2-isocyanatopropionate

HRID 1165169Notes

Reaction equation

HRID 1165169 reaction equation
[N:1](CCC(OCC)=O)=[C:2]=[O:3].[CH2:11]([O:13][C:14](=[O:18])[CH2:15][CH2:16]N)[CH3:12].C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[N:1]([CH:15]([CH3:16])[C:14]([O:13][CH2:11][CH3:12])=[O:18])=[C:2]=[O:3]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 419889Ethyl 3-aminopropanoateHCID 2733373Ethyl 3-isocyanatopropanoate

Product 1

HCID 550681Ethyl 2-isocyanatopropionate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
90 °C

Procedure

The solution of ethyl 3-isocyanatopropionate in toluene used in the above process can be prepared as follows: A mixture of 15.36 g of β-alanine ethyl ester in 600 ml of toluene is dissolved by heating to 90° C. Then 63 ml of a 20% solution of phosgene in toluene are added over 10 minutes under argon and at a temperature of 90°-95° C. Stirring at ca. 90° C. for 16 hours gives the desired solution of ethyl isocyanatopropionate, which is used direct in the above reaction.

Workup

  1. customcan be prepared
  2. dissolutionis dissolved

Sources & evidence

ORD record
ord-d5e43d1d27a64d099410b3c6b8ae9345
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

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