Water → 3-[3-(Benzylthio)-2-oxopropyl]-1,5,5-trimethylimidazolidine-2,4-dione

HRID 32394Notes

Reaction equation

HRID 32394 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][C:17](=[O:29])[CH2:18][N:19]1[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[N:21]([CH3:27])[C:20]1=[O:28].O>CN(C)C=O>[CH2:1]([S:8][CH2:16][C:17](=[O:29])[CH2:18][N:19]1[C:23](=[O:24])[C:22]([CH3:25])([CH3:26])[N:21]([CH3:27])[C:20]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 21699976HCID 21699976, compound

Product 1

HCID 231334523-[3-(Benzylthio)-2-oxopropyl]-1,5,5-trimethylimidazolidine-2,4-dioneYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl mercaptan (256 μl, 2.2 mmol) was stirred with cesium carbonate (712 mg, 2.2 mmol) in dimethyl formamide (5 ml) at room temperature for 1 hour. 3-(3-bromo-2-oxopropyl)-1,5,5-trimethylimidazolidine-2,4-dione (552 mg, 1.99 mmol) prepared as in WO99/06361 was added and the mixture stirred 18 hours at room temperature. The reaction mixture was treated with water, extracted into ethyl acetate (3×25 ml), the organic phases combined, brine washed and dried. The product was purified by silica chromatography, eluting with 50% ethyl acetate/iso-hexane to give 300 mg product.

Workup

  1. additionwas added
  2. extractionextracted into ethyl acetate (3×25 ml)
  3. washbrine washed
  4. customdried
  5. customThe product was purified by silica chromatography
  6. washeluting with 50% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-6e946dd6dcad49b6b3f332608aa64abc
Source dataset
uspto-grants-2008_09
Patent number
US07427631B2

Reaction notes

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