Triethylamine → 1-(4-Chlorobutoxymethyl)-2-bromo-4,5-dichloroimidazole

HRID 979511Notes

Reaction equation

HRID 979511 reaction equation
[Br:1][C:2]1[NH:3][C:4]([Cl:8])=[C:5]([Cl:7])[N:6]=1.C(N(CC)CC)C.[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22]Cl>C1(C)C=CC=CC=1>[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][N:3]1[C:4]([Cl:8])=[C:5]([Cl:7])[N:6]=[C:2]1[Br:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 994842-Bromo-4,5-dichloro-1H-imidazoleHCID 3146301-Chloro-4-(chloromethoxy)butane

Product 1

HCID 137726871-(4-Chlorobutoxymethyl)-2-bromo-4,5-dichloroimidazoleYield 35.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 1.08 g of 2-bromo-4,5-dichloroimidazole, 0.51 g of triethylamine and about 30 ml of toluene was added dropwise 0.79 g of 4-chlorobutoxymethyl chloride at room temperature, and the resulting mixture was stirred at room temperature for 2 hours. The deposited crystal was filtered off and washed with about 10 ml of toluene. The filtrate thus obtained was concentrated under reduced pressure, and the residual oily product was purified by column chromatography on silica gel to obtain 0.60 g of 1-(4-chlorobutoxymethyl)-2-bromo-4,5-dichloroimidazole.

Workup

  1. filtrationThe deposited crystal was filtered off
  2. washwashed with about 10 ml of toluene
  3. customThe filtrate thus obtained
  4. concentrationwas concentrated under reduced pressure
  5. customthe residual oily product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4b56f2c78ab2487fb6f83b09156286ee
Source dataset
uspto-grants-1987_05
Patent number
US04668693

Reaction notes

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