N-Iodosuccinimide → HCID 15230229, compound

HRID 2226169Notes

Reaction equation

HRID 2226169 reaction equation
[CH2:1]([N:8]1[C:14]([CH3:16])([CH3:15])[C:12](=[O:13])[N:11]([CH2:17][C:18]#[CH:19])[C:9]1=[O:10])[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:14]([CH3:15])([CH3:16])[C:12](=[O:13])[N:11]([CH2:17][C:18]#[C:19][I:20])[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 18966551HCID 18966551, compound

Product 1

HCID 15230229HCID 15230229, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-benzyl-3-propargyl-5,5-dimethylhydantoin (1.2 g, 4.6 mmole) in acetone (50 mL) at room temperature was added finely ground silver nitrate (0.15 g. 0.8 mmole), followed by N-iodosuccinimide (1.16 g, 5.2 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 titrate 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 1.5 g of 1-benzyl-3-(3-iodo-2-propynyl)-5,5-dimethylhydantoin as a solid, mp=109°-112° 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 titrate 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-c0fd6277614a497789f1e75a5f6d95e1
Source dataset
uspto-grants-1994_09
Patent number
US05346913

Reaction notes

Loading…