N-bromobutanimide → HCID 9951199, compound

HRID 1451040Notes

Reaction equation

HRID 1451040 reaction equation
C(C1[N:17]2[C:8]([C:9](=[O:25])[NH:10][C:11]3[C:12]([CH2:23][CH3:24])=[N:13][C:14]([N:18]4[CH:22]=[CH:21][N:20]=[CH:19]4)=[N:15][C:16]=32)=[CH:7]N=1)CC=C.Br[N:27]1[C:31](=O)[CH2:30][CH2:29][C:28]1=[O:33].[C:34](O)(=[O:36])C.O>C(O)(=O)C.C([O-])(=O)C.[Ag+]>[OH:33][CH:28]([CH2:34][OH:36])[CH2:29][CH2:30][C:31]1[N:17]2[C:8]([C:9](=[O:25])[NH:10][C:11]3[C:12]([CH2:23][CH3:24])=[N:13][C:14]([N:18]4[CH:22]=[CH:21][N:20]=[CH:19]4)=[N:15][C:16]=32)=[CH:7][N:27]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 9884150HCID 9884150, compoundHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 9951199HCID 9951199, compound

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 176Acetic AcidSolvent

Procedure

Dissolve 5.25 g (15.7 mmol) of the product of Example 9i in 100 mL of acetic acid at 0° C. Add 2.79 g (15.7 mmol) of N-bromosuccinimide and 2.61 g (15.6 mmol) of silver acetate, and stir the mixture at room temperature for 24 h. Add 50 mL of 9/1 acetic acid/water and heat to 90° C. for 16 h. Filter the mixture through Celite, evaporate the solvent, and dissolve the residue in 1N HCl. Treat the solution with charcoal, filter, and make basic with concentrated NH4OH. Collect the precipitate and wash with water and acetonitrile. Suspend the precipitate in 200 mL of 3/1-methanol/concentrated NH4OH and heat to reflux for 8 h. Evaporate the mixture, dissolve the residue in 2N HCl, and precipitate with concentrated NH4OH. Collect the precipitate and wash with water and acetonitrile. Triturate the precipitate with boiling methanol, DMF, and then again with methanol to provide the title compound.

Workup

  1. temperatureheat to 90° C. for 16 h
  2. filtrationFilter the mixture through Celite
  3. customevaporate the solvent
  4. dissolutiondissolve the residue in 1N HCl
  5. additionTreat the solution with charcoal
  6. filtrationfilter
  7. customCollect the precipitate
  8. washwash with water and acetonitrile
  9. temperatureheat
  10. temperatureto reflux for 8 h
  11. customEvaporate the mixture
  12. dissolutiondissolve the residue in 2N HCl
  13. customCollect the precipitate
  14. washwash with water and acetonitrile
  15. customTriturate the precipitate with boiling methanol, DMF

Sources & evidence

ORD record
ord-155c70b86b264ceebdd9d852bbde3a9e
Source dataset
uspto-grants-1997_02
Patent number
US05602252

Reaction notes

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