N-bromobutanimide → HCID 19867087, compound

HRID 1904360Notes

Reaction equation

HRID 1904360 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:13]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]2[CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17]([Br:20])=[C:16]([CH3:18])[N:15]=[C:14]2[CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 71305Nanterinone

Product 1

HCID 19867087HCID 19867087, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred suspension of 8-methyl-6-(2,4-dimethylimidazol1-yl)-2-(1H)-quinolone (0.5 g) in chloroform (10 cm3) was added N-bromosuccinimide (NS) (0.374 g) at room temperature. After 5 minutes the reaction mixture was evaporated to dryness and the residue chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate:methanol, 10:1. Combination and evaporation of the appropriate fractions afforded a solid which on recrystallisation from ethyl acetate/methanol gave 8-methyl-6-(5-bromo-2,4-dimethylimidazol-1-yl)-2-(1m.p. 273°, (0.277 g).

Workup

  1. customAfter 5 minutes the reaction mixture was evaporated to dryness
  2. customthe residue chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  3. washeluting with ethyl acetate
  4. customCombination and evaporation of the appropriate fractions
  5. customafforded a solid which
  6. customon recrystallisation from ethyl acetate/methanol
  7. customgave 8-methyl-6-(5-bromo-2,4-dimethylimidazol-1-yl)-2-(1m.p
  8. custom273°, (0.277 g)

Sources & evidence

ORD record
ord-566a982bf22b48a1b5c9eb5a35f2b224
Source dataset
uspto-grants-1989_06
Patent number
US04837334

Reaction notes

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