N-bromobutanimide → HCID 15616672, compound

HRID 1193624Notes

Reaction equation

HRID 1193624 reaction equation
[CH2:1]([C:3]1[C:4]([S:18][CH3:19])=[N:5][C:6]2[N:7]([CH:10]=[C:11]([C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])[N:12]=2)[C:8]=1[CH3:9])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:20][C:10]1[N:7]2[C:8]([CH3:9])=[C:3]([CH2:1][CH3:2])[C:4]([S:18][CH3:19])=[N:5][C:6]2=[N:12][C:11]=1[C:13](=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15616670HCID 15616670, compound

Product 1

HCID 15616672HCID 15616672, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1.0 g (3.63 mmol) of 1-(6-ethyl-5-methyl-7-methylthioimidazo[1,2-a]pyrimidin-2-yl)-2-methyl-2-propen-1-one in 50 ml of chloroform was treated with 0.71 g (4.0 mmol) of N-bromosuccinimide. After 20 minutes at room temperature, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica, 25 g: dichloromethane) to obtain 1.1 g (87%) of 1-(3-bromo-6-ethyl-5-methyl-7-methylthioimidazo[1,2-a]pyrimidin-2-yl)-2-methyl-2-propen-1-one in the form of pale yellow crystals melting at 87°-9° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (silica, 25 g: dichloromethane)

Sources & evidence

ORD record
ord-6c3c091a4a71466db401ddec071b8555
Source dataset
uspto-grants-1989_03
Patent number
US04810828

Reaction notes

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