Triethylamine → N-Methyl-N-methoxy-2-(1-triphenylmethyl-1H-imidazol-4-yl)acetamide

HRID 342121

Reaktionsgleichung

Reaktionsgleichung von HRID 342121
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([OH:9])=O)[N:3]=[CH:2]1.[C:10]1([C:16](Br)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([N:32]([CH2:35]C)CC)C.Cl.CN(C)CCCN=C=NCC.[C:49](=O)(O)[O-:50].[Na+]>CN(C)C=O.O>[CH3:35][N:32]([O:50][CH3:49])[C:7](=[O:9])[CH2:6][C:4]1[N:3]=[CH:2][N:1]([C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 11692BromotriphenylmethaneHCID 96215Imidazole-4-acetic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 54243787N-Methyl-N-methoxy-2-(1-triphenylmethyl-1H-imidazol-4-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-imidazoleacetic acid (1.04 g, 6.40 mmol) and triphenylmethyl bromide (2.48 g, 7.68 mmol) in dimethylformamide (40 ml) was added triethylamine (4.46 ml, 32 mmol) and the suspension allowed to stir for 18 hours at room temperature. After this time, the mixture was treated with 3-hydroxy-1,2,3-benzotriazin-4(3)-one (HOOBT) (1.31 g, 8 mmol), N, O-dimethylhydroxyamine hydrochloride (1.56 g, 16 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (1.53 g, 8 mmol) and stirred for 24 hours at room temperature. After this time, sat. aq. sodium bicarbonate (50 ml) and water (50 ml) were added and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with sat. aq. NaHCO3 (100 ml) and then brine (50 ml) and the solvent evaporated in vacuo. The residue was suspended in ether (20 ml) and the white solid filtered to give the title compound as a white solid. 1NMR(CD3OD, 300 MHz) δ 7.37(10H, m), 7.16(6H, m), 6.84(1H, s), 3.73(2H, s), 3.68(3H, s) and 3.18(3H, s)ppm.

Aufarbeitung

  1. stirringstirred for 24 hours at room temperature
  2. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  3. washThe combined extracts were washed with sat. aq. NaHCO3 (100 ml)
  4. custombrine (50 ml) and the solvent evaporated in vacuo
  5. filtrationthe white solid filtered

Quellen und Nachweise

ORD-Eintrag
ord-b17ad3e9309c4c468864fcd3b06c7b39
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856326

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