Thionyl Chloride → 5-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 46860

Reaktionsgleichung

Reaktionsgleichung von HRID 46860
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12]O)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.S(Cl)([Cl:18])=O>ClC(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12][Cl:18])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 30173585-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one

Produkt 1

HCID 203856305-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 20 parts of 5-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one, 34 parts of sulfinyl chloride and 300 parts of trichloromethane is stirred and refluxed for 4 hours. The trichloromethane is evaporated and the residue is crystallized from 4-methyl-2-pentanone (activated charcoal). The product is filtered off (the filtrate is set aside), yielding a first fraction of 8.2 parts of 5-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one. The filtrate, which was set aside, is concentrated and the concentrate is stirred with 2,2'-oxybispropane. The precipitated product is filtered off and dried, yielding a second fraction of 8 parts of 5-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one.

Aufarbeitung

  1. temperaturerefluxed for 4 hours
  2. customThe trichloromethane is evaporated
  3. customthe residue is crystallized from 4-methyl-2-pentanone (activated charcoal)
  4. filtrationThe product is filtered off (the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-57b432926f4442278407d58bc68d31a0
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175129

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