Diethyl Ether → HCID 20826174, compound

HRID 586763Notes

Reaction equation

HRID 586763 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=O.CCOCC>ClCCl>[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[C:20]1[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 78498N-Methyl-o-phenylenediamineHCID 5880812,4-Difluorobenzoyl chloride

Product 1

HCID 20826174HCID 20826174, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-methyl-benzene 1,2-diamine (1.22 g, 10 mmol) and 40 ml of dichloromethane were charged in a 250 ml round bottle, 3 ml of triethylamine was then added, and the mixture was cooled to 0° C. 2,4-Difluoro-benzoyl chloride (1.77 g, 10 mmol) was dissolved in 40 ml of dichloromethane and then slowly added to the 250 ml round bottle. The reaction was conducted under a nitrogen atmosphere for 6 hours. After the reaction was complete, ether was added to form precipitation. The solid product was collected by filtration, washed with ether several times, and heated under reduced pressure to form 2-(2,4-difluoro-phenyl)-1-methyl-1H-benzoimidazole (yield=1.97 g, 81%).

Workup

  1. additionwas then added
  2. additionslowly added to the 250 ml round bottle
  3. customto form
  4. customprecipitation
  5. filtrationThe solid product was collected by filtration
  6. washwashed with ether several times
  7. temperatureheated under reduced pressure

Sources & evidence

ORD record
ord-5a82ded31ee14794b70311baf91af3bf
Source dataset
uspto-grants-2005_08
Patent number
US06936716B1

Reaction notes

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