3,5-Dichlorophenyl isocyanate → HCID 14326203, compound

HRID 580509Notes

Reaction equation

HRID 580509 reaction equation
[CH2:1]([NH:4][CH:5]([CH3:10])[C:6]([O:8]C)=O)[CH:2]=[CH2:3].[Cl:11][C:12]1[CH:13]=[C:14]([N:19]=[C:20]=[O:21])[CH:15]=[C:16]([Cl:18])[CH:17]=1>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([N:19]2[C:6](=[O:8])[CH:5]([CH3:10])[N:4]([CH2:1][CH:2]=[CH2:3])[C:20]2=[O:21])[CH:15]=[C:16]([Cl:18])[CH:17]=1

Participants

4

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 19076105HCID 19076105, compound

Product 1

HCID 14326203HCID 14326203, compoundYield 114.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 10.5 g (0.073 mole) of methyl 2-allylaminopropionate in 50 ml of toluene is added 15 g (0.08 mole) of 3,5-dichlorophenylisocyanate in small portions. The resulting mixture is heated to reflux for 2 hours. The reaction mixture is cooled and filtered. The filtrate is concentrated under vacuum to give 25 g of a yellow oil. This material is further purified by passing it through a silica gel column using 40/60 ethyl acetate/hexane as the solvent followed by trituration with hexane/ether to give 18 g of a light yellow solid., m.p. 78°-80°.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-5db9e175ea9f4174ae13a63869871bef
Source dataset
uspto-grants-1988_06
Patent number
US04753957

Reaction notes

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