Triethylamine → 1-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

HRID 267079

Reaktionsgleichung

Reaktionsgleichung von HRID 267079
Cl.[CH3:2][O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1.C(N(CC)CC)C.[C:19]1([C:25](Br)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[CH:8][N:9]([C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:10]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11692BromotriphenylmethaneHCID 178499561HCID 178499561, Verbindung

Produkt 1

HCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 1H-imidazole-4-acetic acid methyl ester hydrochloride (1, 7.48, 42.4 mmol) in methylene chloride (200 ml) was added triethylamine (17.7 ml, 127 mmol) and triphenylmethyl bromide (16.4 g, 50.8 mmol) and stirred for 72 h. After this time, reaction mixture was washed with sat. aq. sodium bicarbonate (100 ml) and water (100 ml). The organic layer was evaporated in vacuo and purified by flash chromatography (30-100% ethyl acetate/hexanes gradient elution) to provide 23 as a white solid.

Aufarbeitung

  1. customAfter this time, reaction mixture
  2. washwas washed with sat. aq. sodium bicarbonate (100 ml) and water (100 ml)
  3. customThe organic layer was evaporated in vacuo
  4. custompurified by flash chromatography (30-100% ethyl acetate/hexanes gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-8eab64f6cb12427ab25dc8ec6d161a68
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652257

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