4-Iodo-1-tritylimidazole → HCID 59749576, Verbindung

HRID 747258Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747258
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.CON(C)[C:33]([C:35]1[C:40]2=[N:41][S:42][N:43]=[C:39]2[CH:38]=[CH:37][CH:36]=1)=[O:34]>ClCCl>[N:43]1[S:42][N:41]=[C:40]2[C:35]([C:33]([C:2]3[N:3]=[CH:4][N:5]([C:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:6]=3)=[O:34])=[CH:36][CH:37]=[CH:38][C:39]=12

Komponenten

5

Edukt 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 59749564Benzo[1,2,5]thiadiazole-4-carboxylic acid methoxy-methyl-amideHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 59749576HCID 59749576, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 4-iodo-1-tritylimidazole (commercially available from Synchem) (6.3 g, 14.4 mmol) in dichloromethane (100 mL) at rt was treated with ethyl magnesium bromide (4.8 mL, 14.4 mmol, 3M in THF) and allowed to react for 1 h. A solution of benzo[1,2,5]thiadiazole-4-carboxylic acid methoxy-methyl-amide (Intermediate L2) (2.0 g, 9.0 mmol) in dichloromethane (50 mL) was added via syringe at rt and stirred for 40 m. The residue was isolated in a typical aqueous workup and purified by chromatography on silica gel with 30% EtOAc:hexane to give benzo[1,2,5]thiadiazol-4-yl-(1-trityl-1H-imidazol-4-yl)-methanone (Intermediate L3), 1 g (25%).

Aufarbeitung

  1. customto react for 1 h
  2. customThe residue was isolated in a typical aqueous workup
  3. custompurified by chromatography on silica gel with 30% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b60f56f9b1e2412daf19f48660eda6e0
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396849B2

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