Acetone → HCID 15227706, compound

HRID 2226164Notes

Reaction equation

HRID 2226164 reaction equation
[CH2:1]([N:4]1[C:8](=[O:9])[C:7]([CH3:11])([CH3:10])[NH:6][C:5]1=[O:12])[C:2]#[CH:3].[I:13]N1C(=O)CCC1=O.CC(C)=O>C(Cl)(Cl)(Cl)Cl.O.[N+]([O-])([O-])=O.[Ag+]>[I:13][C:3]#[C:2][CH2:1][N:4]1[C:8](=[O:9])[C:7]([CH3:10])([CH3:11])[NH:6][C:5]1=[O:12]

Participants

7

Reactant 3

HCID 180AcetoneHCID 120273N-IodosuccinimideHCID 3028675HCID 3028675, compound

Product 1

HCID 15227706HCID 15227706, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 3-(2-propynyl)-5,5-dimethylhydantoin (1 g, 60 mmole) in CCl4 (20 mL) at room temperature was added N-iodosuccinimide (1.6 g, 7.1 mmole). Dry acetone was added until all materials were dissolved. To the above clear solution was added silver nitrate (0.1 g, 0.58 mmole) and the reaction mixture was stirred at room temperature for 2 hr. The mixture was diluted with water (60 mL) and was extracted with ethyl acetate (3×50 mL). The organic layer was washed with saturated sodium chloride solution (75 mL) and dried with sodium sulfate. After filtering off drying agent and evaporating the solvents, a light yellow solid of 3-(3-iodo-2-propynyl)-5,5-dimethylhydantoin was obtained, 1.6 g (91%), mp=118°-126° C. An NMR spectrum also showed the desired product.

Workup

  1. dissolutionwere dissolved
  2. extractionwas extracted with ethyl acetate (3×50 mL)
  3. washThe organic layer was washed with saturated sodium chloride solution (75 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationAfter filtering off
  6. customdrying agent
  7. customevaporating the solvents

Sources & evidence

ORD record
ord-880b1a2c05e44545aa4b287c304d0c11
Source dataset
uspto-grants-1994_09
Patent number
US05346913

Reaction notes

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