Azobisisobutyronitrile → HCID 53938046, compound

HRID 1250140Notes

Reaction equation

HRID 1250140 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5](=[CH:10][O:11][CH3:12])[C:6]([O:8][CH3:9])=[O:7].[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5](=[CH:10][O:11][CH3:12])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 838711HCID 838711, compound

Product 1

HCID 53938046HCID 53938046, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2.2 g of methyl 2-(2-methylphenoxy)-3-methoxyacrylate, 1.78 g of N-bromosuccinimide, and a catalytic amount of azobisisobutyronitrile was heated at reflux in carbon tetrachloride for 4 hours. The solid was filtered, and the solvent evaporated to give crude methyl 2-(2-bromomethylphenoxy)-3-methoxyacrylate. A mixture of this crude material, 2.0 g of N-benzyloxy propionamide, and 3.9 g of caesium carbonate was heated at reflux in acetonitrile for 20 hours. The solid was filtered, the solvent evaporated, and the residue purified by silica gel chromatography to give methyl 2-{2-[(1-benzyloxyiminopropyl)oxymethyl]phenoxy}-3-methoxyacrylate (isomer Z) (0.75 g).

Workup

  1. filtrationThe solid was filtered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-9bdc1cd7be07478e8b3c3c3d54146f29
Source dataset
uspto-grants-2002_01
Patent number
US06337306B1

Reaction notes

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