Ammonium → HCID 178488386, compound

HRID 530416Notes

Reaction equation

HRID 530416 reaction equation
[CH:1]1([N:7]2[C:11](=[O:12])[C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[NH:9][C:8]2=S)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+:30].C(OO)(C)(C)C>CO>[CH:1]1([N:7]2[C:11](=[O:12])[C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[NH:9][C:8]2=[NH:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 223AmmoniumHCID 6410tert-Butyl hydroperoxideHCID 76335704HCID 76335704, compound

Product 1

HCID 178488386HCID 178488386, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-cyclohexyl-5,5-bis(4-methoxyphenyl)-2-thioxoimidazolidin-4-one (3.0 g, 7.3 mmol) in methanol was added aqueous ammonium (25%, 40 mL) and tert-butyl hydroperoxide (70%, 10 mL) separately, and the resulting solution was stirred at room temperature overnight. The mixture was extracted with dichloromethane and the organic layer was concentrated in vacuo. The residue was purified over a silica column to give the title compound as a white solid (1.7 g, 59% two steps). 1H NMR (400 MHz, d6-DMSO) δ 7.25 (d, J=8.0 Hz, 4H), 6.84 (d, J=7.6 Hz, 4H), 6.47 (s, 1H), 3.71 (s, 6H), 3.70 (s, 1H), 2.09 (m, 2H), 1.74 (m, 2H), 1.52-1.60 (m, 3H), 1.26 (m, 2H), 1.13 (m, 1H). LC-MS m/z 394.2 (M+H).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. concentrationthe organic layer was concentrated in vacuo
  3. customThe residue was purified over a silica column

Sources & evidence

ORD record
ord-7296950c75b941218830ce643bee9fab
Source dataset
uspto-grants-2016_05
Patent number
US09353089B2

Reaction notes

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