N-bromobutanimide → HCID 53833858, compound

HRID 1608666Notes

Reaction equation

HRID 1608666 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[N:7]=[C:8]([CH3:11])[S:9][CH:10]=1)([OH:3])=[O:2].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:19][CH2:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])[N:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19697485HCID 19697485, compound

Product 1

HCID 53833858HCID 53833858, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirring solution of 4-carboxyethyl-2-methyl thiazole (30.3 g) in CCl4 (1L) was added NBS (37.7 g) and AIBN (2.2 g). The resulting mixture was refluxed and irradiated with UV light for 4 hours. The mixture was cooled to room temperature and filtered. The solution was flash chromatographed (CH2Cl2) to yield 36.6 g of a red oil. This material was used without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. customirradiated with UV light for 4 hours
  3. filtrationfiltered
  4. customchromatographed (CH2Cl2)

Sources & evidence

ORD record
ord-e5336834a3324b6b99d2e521fb3b8c4a
Source dataset
uspto-grants-1995_03
Patent number
US05395932

Reaction notes

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