反応 #44820

反応方程式

isothiocyanate

thiourea

thiophosgene

dicyclohexylcarbodiimide

NaHCO3

→

2-aminobenzimidazole

溶媒

THF

dichloromethane

反応条件

後処理

1. 1
   その他prepared
2. 2
   その他evaporated to dryness
3. 3
   その他The resulting thiourea was then purified by e.g. column chromatography
4. 4
   その他reacted further as crude material
5. 5
   workup.STIRRINGstirred
6. 6
   温度at reflux temperature overnight
7. 7
   抽出the solution extracted with EtOAc
8. 8
   乾燥The combined organic phases were dried (MgSO4)
9. 9
   ろ過filtered
10. 10
    濃縮concentrated in vacuo

実験手順

A mixture of an isothiocyanate (prepared by reacting the corresponding amine with thiophosgene) and a suitably substituted phenylenediamine in dry dichloromethane was stirred at rt overnight and evaporated to dryness. The resulting thiourea was then purified by e.g. column chromatography or reacted further as crude material. Thus, the thiourea was dissolved in THF, added a coupling reagent such as dicyclohexylcarbodiimide (DCC), and stirred at reflux temperature overnight. Aqueous NaHCO3 was added and the solution extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the crude 2-aminobenzimidazole which was subsequently purified by column chromatography or preparative LCMS.

出典