Iodoethane → HCID 58424322, compound

HRID 1408584Notes

Reaction equation

HRID 1408584 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=[S:17])[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:30](I)[CH3:31].[CH3:33][C:34]#N>>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[N:14]([CH2:33][CH3:34])[C:13]([S:17][CH2:30][CH3:31])=[N:12]3)[CH2:10][CH:9]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 58423943HCID 58423943, compound

Product 1

HCID 58424322HCID 58424322, compoundYield 69%

Procedure

To a mixture of 6-bromo-2-phenyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (250 mg, 0.64 mmol) and K2CO3 (356 mg, 2.6 mmol) in CH3CN (8 mL) was added EtI (402 mg, 2.6 mmol). The reaction mixture refluxed for 2 h. The mixture was filtered, and the filtrate was concentrated to give a residue, which was purified by preparative TLC to give 6-bromo-1′-ethyl-2′-(ethylthio)-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (195 mg, 69%).

Workup

  1. temperatureThe reaction mixture refluxed for 2 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give a residue, which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-15dac580e615458e869da1950db7ebbb
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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