N-Iodosuccinimide → HCID 15230228, compound

HRID 2226168Notes

Reaction equation

HRID 2226168 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11]([CH3:15])([CH3:14])[N:10]([CH2:16][C:17]#[CH:18])[C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:20]N1C(=O)CCC1=O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([N:8]1[C:12](=[O:13])[C:11]([CH3:14])([CH3:15])[N:10]([CH2:16][C:17]#[C:18][I:20])[C:9]1=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 18966554HCID 18966554, compound

Product 1

HCID 15230228HCID 15230228, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 3-benzyl-1-propargyl-5,5-dimethylhydantoin (2 g, 7.81 mmole) in acetone (35 mL) at room temperature was added N-iodosuccinimide (2.1 g, 9.2 mmole), followed by silver nitrate (0.265 g, 1.56 mmole). The reaction mixture was stirred at room temperature for 5 hr. The reaction mixture was then passed through Celite by suction-filtration and washed with acetone. The filtrate was concentrated on a rotary evaporator and diluted with ethyl acetate. The solution was washed with water and brine and dried over sodium sulfate. The solvent was evaporated on a rotary evaporator to give 1.9 g of 3-benzyl-1-(3-iodo-2-propynyl)-5,5-dimethylhydantoin as a light brown oil which slowly solidified, mp=83°-85° C. An NMR spectrum also showed the desired structure.

Workup

  1. filtrationThe reaction mixture was then passed through Celite by suction-filtration
  2. washwashed with acetone
  3. concentrationThe filtrate was concentrated on a rotary evaporator
  4. additiondiluted with ethyl acetate
  5. washThe solution was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-d197d678719e47c79d912bde5207050e
Source dataset
uspto-grants-1994_09
Patent number
US05346913

Reaction notes

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