Hydrochloric Acid → 5-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-imidazolidine-2,4-dione

HRID 1985216

Reaction equation

HRID 1985216 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[NH:8][C:7](=[O:9])[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[C:5]1=[O:18].N1C=CN=C1.[Si:24](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CN(C=O)C.[Cl-].[Na+].O.C(OCC)C>[C:37]([Si:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[O:1][CH2:2][CH2:3][CH:4]1[NH:8][C:7](=[O:9])[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[C:5]1=[O:18])([CH3:40])([CH3:38])[CH3:39]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 577189415-(2-Hydroxy-ethyl)-3-(4-methyl-benzyl)-imidazolidine-2,4-dione

Product 1

HCID 577192895-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-imidazolidine-2,4-dioneYield 49.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of crude 5-(2-hydroxy-ethyl)-3-(4-methyl-benzyl)-imidazolidine-2,4-dione (24.68 g, 99.4 mmol) and imidazole (10.15 g, 0.149 mol) in DMF (250 mL) was treated dropwise with tert-butyldiphenylsilyl chloride (27.37 g, 99.6 mmol) and then stirred at room temperature under N2 for 7 h. The reaction was worked up extractively with aqueous 1 N HCl (300 mL), diethyl ether and brine and the organic layer was dried (MgSO4) and the solvent removed in vacuo to give crude product which was purified by flash chromatography using a gradient of 5:1 to 2:1 hexanes:EtOAc to afford 23.82 g (49%) of 5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-imidazolidine-2,4-dione. MS (ES+) Calc'd for C29H35N2O3Si (M+1) 487. Found m/z 487 (100%). 1H NMR.

Workup

  1. dry with materialthe organic layer was dried (MgSO4)
  2. customthe solvent removed in vacuo
  3. customto give crude product which
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-1b4b11127b2d483ebbddf1bedb3d7ec9
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Linked notes

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