1,4-Dibromo-2-butyne → 1-(4-Bromo-2-butyn-1-yl)-5, 6-dichloro-3-ethyl-2-methylbenzimidazolium bromide

HRID 354592

Reaction equation

HRID 354592 reaction equation
[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]2[N:6]([CH2:10][CH3:11])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.[Br:15][CH2:16][C:17]#[C:18][CH2:19]Br>CCOCC>[Br-:15].[Br:15][CH2:16][C:17]#[C:18][CH2:19][N+:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[C:13]([Cl:14])=[CH:12][C:5]=2[N:6]([CH2:10][CH3:11])[C:7]=1[CH3:9]

Participants

4

Reactant 2

HCID 752051,4-Dibromo-2-butyneHCID 767171H-Benzimidazole, 5,6-dichloro-1-ethyl-2-methyl-

Product 1

HCID 867388101-(4-Bromo-2-butyn-1-yl)-5, 6-dichloro-3-ethyl-2-methylbenzimidazolium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5,6-Dichloro-1-ethyl-2-methylbenzimidazole (11.5 g., 0.05 moles) and 1,4-dibromo-2-butyne (31 g., 0.15 moles) were mixed together and stirred at room temperature overnight. The reaction mixture was treated with ether, the solid was collected by filtration, washed with ether and dried. It was recrystallized from acetonitrile containing 5% water (400 ml). The product was recovered in two crops. Yield 20.2 g (92%), mp. 185°-189° C.

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with ether
  3. customdried
  4. customIt was recrystallized from acetonitrile containing 5% water (400 ml)
  5. customThe product was recovered in two crops

Sources & evidence

ORD record
ord-2a5f7d380d3e4f4693277dabeadcca5f
Source dataset
uspto-grants-1983_03
Patent number
US04375508

Linked notes

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