Reaktionsgleichung
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12][OH:13])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([OH:26])(=[O:9])=[O:25].[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12][OH:13])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred and cooled (ice-water bath) mixture of 14.1 parts of 5-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one, 8 parts of N,N-diethylethanamine and 195 parts of dichloromethane are added dropwise 7.8 parts of methanesulfonyl chloride. Upon completion, stirring is continued first for 15 minutes while still cooling an further for 1 hour at reflux temperature. The dichloromethane is evaporated and the residue is dissolved in 4-methyl-2-pentanone and water while heating. The layers are separated and the organic phase is stirred with 100 parts of water, while cooling in an ice-bath. The precipitated product is filtered off and dried, yielding 10 parts (53%) of 5-chloro-1,3-dihydro-1-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate; mp. 140° C.
Aufarbeitung
- temperaturecooled
- stirringUpon completion, stirring
- temperaturewhile still cooling an further for 1 hour
- temperatureat reflux temperature
- customThe dichloromethane is evaporated
- dissolutionthe residue is dissolved in 4-methyl-2-pentanone
- temperaturewater while heating
- customThe layers are separated
- stirringthe organic phase is stirred with 100 parts of water
- temperaturewhile cooling in an ice-bath
- filtrationThe precipitated product is filtered off
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-0d8391c82be84a1fa91c49c9758ef615
- Quelldatensatz
- uspto-grants-1979_11
- Patentnummer
- US04175129
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