1-Bromo-3-chloropropane → 1-(3-chloropropyl)-2-methyl-1H-benzimidazole

HRID 1482576

Reaktionsgleichung

Reaktionsgleichung von HRID 1482576
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[OH-].[Na+].[Cl:13][CH2:14][CH2:15][CH2:16]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:13][CH2:14][CH2:15][CH2:16][N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[CH3:1]

Komponenten

6

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 119842-MethylbenzimidazoleHCID 14798Sodium Hydroxide

Produkt 1

HCID 212393601-(3-chloropropyl)-2-methyl-1H-benzimidazoleAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-methyl-1H-benzimidazole (13.2 g, 0.10 mol) was dissolved into 200 ml of 20% wt. sodium hydroxide, 3-chlorobromopropane (31.4 g, 0.20 mol) and tetrabutyl ammonium bromide (1.0 g) were added, and mixed for 5 min. The mixture was heated to 60° C., stirred to react for 2 hours. Then the reaction solution was cooled down to ambient temperature, 100 ml of dichloromethane was added for extraction and liquid separation. To the aqueous phase, 100 of dichloromethane was added for extraction. Organic phases were mixed, washed with 100 ml of saturated saline. Liquid was separated, and organic phase was evaporated to dryness to produce oily product. Oily products were separated and purified by chromatography with neutral Al2O3 to produce 12.9 g of 1-(3-chloropropyl)-2-methyl-1H-benzimidazole, with a yield of 62.1%.

Aufarbeitung

  1. additionwere added
  2. additionmixed for 5 min
  3. customto react for 2 hours
  4. temperatureThen the reaction solution was cooled down to ambient temperature
  5. additionOrganic phases were mixed
  6. washwashed with 100 ml of saturated saline
  7. customLiquid was separated
  8. customorganic phase was evaporated to dryness
  9. customto produce oily product
  10. customOily products were separated
  11. custompurified by chromatography with neutral Al2O3

Quellen und Nachweise

ORD-Eintrag
ord-a52e6e614df043b19ce775c816ab460d
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09415047B2

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