Triethylamine → 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate

HRID 971736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971736
[Cl:1][C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH2:13][OH:14])[C:8](=[O:15])[NH:7][C:6]=2[CH:5]=[CH:4][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:14])=[O:25].[Cl:1][C:2]1[C:10]2[N:9]([CH2:11][CH2:12][CH2:13][OH:14])[C:8](=[O:15])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 203855604-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one

Produkt 1

HCID 867353584-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 9 parts of 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one, 7 parts of N,N-diethylethanamine and 130 parts of dichloromethane are added dropwise 12 parts of methanesulfonyl chloride (exothermic reaction: temperature rises to reflux). Upon completion, stirring is continued for 1 hour at reflux temperature. The reaction mixture is cooled and poured onto water. The organic phase is separated, washed with acidified water, dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone, yielding 9 parts (75%) of 4-chloro-1,3-dihydro-3-(3-hydroxypropyl)-2H-benzimidazol-2-one methanesulfonate.

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. customThe organic phase is separated
  5. washwashed with acidified water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from 4-methyl-2-pentanone

Quellen und Nachweise

ORD-Eintrag
ord-4cc1875c3c7a4dce9fcfc61e44aeec2b
Quelldatensatz
uspto-grants-1979_07
Patentnummer
US04160836

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