N-bromobutanimide → HCID 9951199, compound

HRID 377507Notes

Reaction equation

HRID 377507 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 ambient temperature for 24 hours. Add 500 mL of 9/1 acetic acid/water and heat to 90° C. for 16 hours. Filter the mixture through Celite, evaporate the solvent, and dissolve the residue in 1 N 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 hours. 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 hours
  2. filtrationFilter the mixture through Celite
  3. customevaporate the solvent
  4. dissolutiondissolve the residue in 1 N 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 hours
  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-20a01b9a8b9f459fa8f5b710d147cb0c
Source dataset
uspto-grants-2000_02
Patent number
US06025489

Reaction notes

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