Azobisisobutyronitrile → HCID 13764098, compound

HRID 538589Notes

Reaction equation

HRID 538589 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7]Br)=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.C1C(=O)N(Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 44627631HCID 44627631, compound

Product 1

HCID 13764098HCID 13764098, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of 5-Bromo-2-bromomethyl-4-(4-methoxy-phenyl)-thiazole (5.0 g, 24.3 mmol) in the 20 ml of CCl4 was added NBS (4.32 g, 24.3 mmol) and AIBN (0.4 g, 2.43 mmol). The reaction mixture was heated at 100° C. for 2 h under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (230-400 M) using 1% ethyl acetate/hexane eluent to give the desired product (4.0 g, 58%).

Workup

  1. customAfter the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure
  2. customthe residue was purified by column chromatography on silica (230-400 M)

Sources & evidence

ORD record
ord-4c0a4836a4794a48ae2effa510f294fe
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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