4-Nitrobenzenethiol → 2-[(4-Nitrophenyl)sulfanyl]-1H-benzimidazole

HRID 55080

Reaktionsgleichung

Reaktionsgleichung von HRID 55080
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1)([O-:13])=[O:12].C1CCN2C(=NCCC2)CC1>C(O)C>[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([S:20][C:2]2[NH:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 158094-NitrobenzenethiolHCID 785722-ChlorobenzimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 126176252-[(4-Nitrophenyl)sulfanyl]-1H-benzimidazoleAusbeute 15,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Chlorobenzimidazole (0.033 moles, 5.0 g), 4-nitrothiophenol (0.033 moles, 4.14 g), and DBU (0.033 moles, 5.0 g) in 200 ml ethanol were heated at 55° C. for 3 hr. The reaction was concentrated, ethyl acetate added, washed with water, dried over sodium sulfate and the solvent removed. The solid was slurred in hexane to yield 2-(4-nitrophenylthio)benzimidazole 1.37 g, 15%. Mass Spec (FD) 271. Calculated for C13H8N3O2S: C, 57.55; H, 3.34; N, 15.49. Found: C, 57.50; H, 5.54; N, 15.23.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. additionethyl acetate added
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-e19f3c68bd474193823c5cefc616e6b8
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624937

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