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

HRID 1985216

반응식

HRID 1985216 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1b4b11127b2d483ebbddf1bedb3d7ec9
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544812B2

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