N-bromobutanimide → HCID 67175416, compound

HRID 2233537Notes

Reaction equation

HRID 2233537 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.ClC1C=C(C=CC=1)C(OO)=O>[Br:12][C:3]1[C:2]([CH3:1])=[CH:11][C:6]2=[N:7][C:8](=[O:10])[N:9]=[C:5]2[CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2231345-Methylbenzimidazolone

Product 1

HCID 67175416HCID 67175416, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 70297m-Chloroperbenzoic acidCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6-methyl-1,3-dihydro-benzoimidazol-2-one (1.00 g, 6.76 mmol) as prepared in Example 1, N-bromosuccinimide (1.30 g, 7.30 mmol) and 3-chloroperoxybenzoic acid (0.05 g, 0.29 mmol) in carbon tetrachloride (15 ml) was heated under reflux for 4 h. When cooled to room temperature, the mixture was filtered and the solid was recrystallised from methanol to give (17) as a beige solid (0.80 g). Furthermore, the solid insoluble in methanol was collected to give more (17) (0.50 g) and the solids were combined (1.30 g, 85%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. filtrationthe mixture was filtered
  4. customthe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-1d31a5dc670649dfbe66372a0220f0df
Source dataset
uspto-grants-2010_05
Patent number
US07709514B2

Reaction notes

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