Benzyl Bromide → HCID 19814260, compound

HRID 466606Notes

Reaction equation

HRID 466606 reaction equation
[CH2:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)C(=O)[C:4](=[O:13])[N:3]1[S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-:33].[K+].[K+]>C(C(C)=O)C(C)C>[CH2:24]([N:9]1[CH2:10][CH2:11][C:6]2([O:13][C:4](=[O:33])[N:3]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:15])=[O:16])[C:2]2=[CH2:1])[CH2:7][CH2:8]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19814323HCID 19814323, compound

Product 1

HCID 19814260HCID 19814260, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture containing 3.2 g of 4-methylene-2-oxo-3-(4-toluenesulfonyl)-1-oxo-3,8-diazaspiro[4,5]decane, 2.1 g of benzyl bromide and 1.7 g of anhydrous potassium carbonate in 32 ml of methyl isobutyl ketone is refluxed under nitrogen while stirring for 8 hours. After cooling down the reaction mixture to room temperature the inorganic salts are filtered off and the filtrate is evaporated under reduced pressure. The residue is dissolved in 50 ml of benzene, washed to bromide-free and neutral with water, dried over anhydrous sodium sulfate fate and evaporated under reduced pressure. After recrystallizing the crude product obtained from ethanol the title substance is obtained in 84% yield, m.p.: 157°-158° C.

Workup

  1. temperatureis refluxed under nitrogen
  2. filtrationare filtered off
  3. customthe filtrate is evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in 50 ml of benzene
  5. washwashed to bromide-free and neutral with water
  6. dry with materialdried over anhydrous sodium sulfate fate
  7. customevaporated under reduced pressure
  8. customAfter recrystallizing the crude product
  9. customobtained from ethanol the title substance
  10. customis obtained in 84% yield, m.p.: 157°-158° C.

Sources & evidence

ORD record
ord-31f8c22376124ac5ad3c9aa097256cc2
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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