1,1'-Carbonyldiimidazole → 4-(2,2-Dimethoxyethyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 730569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730569
[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:6]=1[NH2:12].[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16]>>[CH3:14][O:13][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[C:6]2[NH:12][C:15](=[O:16])[NH:11][C:7]=2[CH:8]=[CH:9][CH:10]=1

Komponenten

3

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 578350073-(2,2-Dimethoxyethyl)benzene-1,2-diamine

Produkt 1

HCID 578349714-(2,2-Dimethoxyethyl)-1,3-dihydro-2H-benzimidazol-2-oneAusbeute 38 %

Versuchsvorschrift

3-(2,2-Dimethoxy-ethyl)-benzene-1,2-diamine (1.03 g, 5.26 mmol) was dissolved in dTHF and carbonyldiimidazole (935 mg, 5.77 mmol) added. The mixture was stirred at rt for 18 hours. The solvent was removed and the crude material chromatographed to afford 4-(2,2-dimethoxy-ethyl)-1,3-dihydro-benzoimidazol-2-one as a colorless solid (440 mg, 38%). 1H NMR (CDCl3) δ 3.03 (2H, d, J=5.2 Hz), 3.40 (6H, s), 4.58 (1H, t, J=5.2 Hz), 6.86-6.89 (m, 1H), 6.96-7.02 (m, 2H), 9.29 (br s, 1H), 10.28 (br s, 1H). MS: 221 (M−H)−.

Aufarbeitung

  1. additionadded
  2. customThe solvent was removed
  3. customthe crude material chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-96458dcbcc71431b963f33d4814c1cef
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582760B2

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