Azobisisobutyronitrile → HCID 53960446, compound

HRID 1492926Notes

Reaction equation

HRID 1492926 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][CH:7]=[C:8]([C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=1.[Br:19]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][CH:7]=[C:8]([C:9](=[CH:14][O:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 53747278HCID 53747278, compound

Product 1

HCID 53960446HCID 53960446, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 71 g of methyl α-(5-methyl-3-benzo[b]thienyl)-β-methoxyacrylate (see Example 1 ), 57.8 g of N-bromosuccinimide, 1.1 g of azodiisobutyronitrile and 720 ml of carbon tetrachloride is refluxed for 75 minutes. The mixture is cooled to room temperature and filtered, and the filtrate is then concentrated under reduced pressure, and the yellow oil which remains is purified by chromatography on silica gel using diethyl ether/n-hexane (1:1). The crude product is crystallized from methylene chloride/n-hexane, and methyl α-(5-bromomethyl-3-benzo[b]thienyl)-β-methoxyacrylate is obtained in this manner as pale yellow crystals, m.p. 124°-125° C.

Workup

  1. temperatureis refluxed for 75 minutes
  2. filtrationfiltered
  3. concentrationthe filtrate is then concentrated under reduced pressure
  4. customthe yellow oil which remains is purified by chromatography on silica gel
  5. customThe crude product is crystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-3efe498806044965b4be7274661ecb7d
Source dataset
uspto-grants-1994_12
Patent number
US05376677

Reaction notes

Loading…