Methyl iodide → HCID 58424476, compound

HRID 1408768Notes

Reaction equation

HRID 1408768 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.[OH-].[Na+].CI>CO>[CH2:9]([N:14]1[C:15](=[O:16])[C:11]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[O:8][CH:9]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:10]2)[N:12]=[C:13]1[S:17][CH2:11][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 58423943HCID 58423943, compound

Product 1

HCID 58424476HCID 58424476, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-2-phenyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (110 mg, 0.28 mmol) in MeOH (5 mL) in a 10 mL CEM microwave test tube is added a 0.6 N NaOH aqueous solution (1.0 mL). After stirring at rt for 10 min, MeI (158 mg, 1.08 mmol) is added, and the reaction is continued with stirring at rt for 2 hrs. Upon removing the solvent in vacuo, the residue is purified by flash chromatography column to give 1′-benzyl-2′-(benzylthio)-6-bromo-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (63.3 mg, 39%). MS m/z 569 (M+H+).

Workup

  1. stirringwith stirring at rt for 2 hrs
  2. customUpon removing the solvent in vacuo
  3. customthe residue is purified by flash chromatography column

Sources & evidence

ORD record
ord-ad0de996d0974867a0f5932e8f7dcde5
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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