Diethyl Ether → N-(1-tert-butoxycarbonyl-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthiourea

HRID 1736457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1736457
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:18]=[C:19]=[S:20])=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:24])[CH2:22][NH2:23].CCOCC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:23][CH2:22][CH2:21][NH2:24])=[S:20])=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 3301EthylenediamineHCID 214727251h-Benzimidazole-1-carboxylic acid,5-isothiocyanato-4-methyl-,1,1-dimethylethyl ester

Produkt 1

HCID 21472715N-(1-tert-butoxycarbonyl-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-tert-butoxycarbonyl-4-methyl-5-benzimidazolylisothiocyanate (7.0 g) in CH2Cl2 (600 mL) is added dropwise over 45 minutes to ethylenediamine (8 mL) in solution in CH2Cl2 (200 mL). The mixture is stirred for 3 hours at room temperature. Ether (150 mL) is added to the suspension and the mixture is stirred for 10 minutes at room temperature. The solid is filtered. The filtrate is rotary evaporated, the residue diluted with CH2Cl2 and reprecipitated with ether to afford a second crop. The combined solids are dried overnight in vacuo to afford N-(1-tert-butoxycarbonyl-4-methyl-5-benzimidazolyl)-N'-2-aminoethylthiourea as a white solid.

Aufarbeitung

  1. stirringthe mixture is stirred for 10 minutes at room temperature
  2. filtrationThe solid is filtered
  3. additionthe residue diluted with CH2Cl2
  4. customreprecipitated with ether
  5. customto afford a second crop
  6. customThe combined solids are dried overnight in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bf858e682aad408b9cd89cdaa78a4c0a
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05541210

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