Methyl iodide → HCID 58423987, compound

HRID 1408651Notes

Reaction equation

HRID 1408651 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=O)[NH:14][C:13](=[S:17])[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[C:25]([O-:28])([O-])=O.[K+].[K+].[CH3:31]I>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:25](=[O:28])[N:14]([CH3:15])[C:13]([S:17][CH3:31])=[N:12]3)[CH2:10][CH:9]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58424170HCID 58424170, compound

Product 1

HCID 58423987HCID 58423987, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 6-bromo-2-(4-chlorophenyl)-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (450 mg, 1.07 mmol) and K2CO3 (588 mg, 4.27 mmol) in CH3CN (10 mL) was added MeI (610 mg, 4.27 mmol). The reaction mixture was 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-2-(4-chlorophenyl)-1′-methyl-2′-(methylthio)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (325 mg, 37%). 1H-NMR (CDCl3): 1.89 (m, 1H), 2.41 (m, 1H), 2.56 (t, 3H), 3.17 (m, 3H), 5.81 (m, 1H), 6.79 (m, 2H), 7.23 (m, 1H), 7.43 (m, 4H).

Workup

  1. temperatureThe reaction mixture was 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-1e260ebe88b84e05b917cbe430e53de2
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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