Sodium Hydroxide → 1-(3-chloro-2-methylpropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

HRID 46868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46868
[CH3:1][C:2]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])=[CH2:3].[OH-].[Na+].Br[CH2:17][CH:18]([CH3:21])[CH2:19][Cl:20]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:20][CH2:19][CH:18]([CH3:21])[CH2:17][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([C:2]([CH3:1])=[CH2:3])[C:5]1=[O:13]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 955661-Bromo-3-chloro-2-methylpropaneHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Produkt 1

HCID 205062821-(3-chloro-2-methylpropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-oneAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 66133Benzyl triethylammonium chlorideKatalysator

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a stirred mixture of 17.4 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one, 5-parts of N,N,N-triethyl benzenemethanaminium chloride and 180 parts of sodium hydroxide solution 60% are added dropwise 21 parts of 1-bromo-3-chloro-2-methylpropane while heating at 55° C. Upon completion, stirring at 55° C. is continued for 3 hours. The reaction mixture is cooled, poured onto water and the product is extracted with methylbenzene. The extract is dried, filtered and evaporated, yielding 24 parts (90.6%) of 1-(3-chloro-2-methylpropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one as a residue.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto water
  3. extractionthe product is extracted with methylbenzene
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b87cf91db1f1412586dd18038036ec83
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175129

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