N-bromobutanimide → HCID 18928115, compound

HRID 1599411Notes

Reaction equation

HRID 1599411 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:16]([CH3:24])=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=2.[Br:25]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:25][CH2:24][C:16]1[N:4]2[C:5]3[C:10]([N:11]=[C:2]([Cl:1])[C:3]2=[N:18][C:17]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:9][C:8]([C:12]([F:15])([F:13])[F:14])=[CH:7][CH:6]=3

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 18928110HCID 18928110, compound

Product 1

HCID 18928115HCID 18928115, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-chloro-2-ethoxycarbonyl-1-methyl-7-trifluoromethylimidazo[1,2-a]quinoxaline (830 g, 232 mmol), N-bromosuccinimide (68,0 g, 382 mmol) and 2,2'-azobis(2-methylpropionitrile)(200 mg, 1.2 mmol) in tetrachloromethane (1.5 l) was heated at reflux for 18 h, allowed to cool and the product collected by filtration. The product was dissolved in dichloromethane (2 l) and washed with water, dried (MgSO4), followed by purification with silica gel 60 (1 g). The organic phase was filtered and evaporated in vacuo. The residue was suspended in petroleum ether to yield 91.7 g (91%) of 1-bromomethyl-4-chloro-2-ethoxycarbonyl-7-trifluoromethyl-imidazo[1,2-a]quinoxaline which was collected by filtration. M.p. 196°-198° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureto cool
  4. filtrationthe product collected by filtration
  5. dissolutionThe product was dissolved in dichloromethane (2 l)
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. customfollowed by purification with silica gel 60 (1 g)
  9. filtrationThe organic phase was filtered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-fcf60b5290644ab5bc1db9f9532aa232
Source dataset
uspto-grants-1998_04
Patent number
US05741785

Reaction notes

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