Diethyl Ether → HCID 20826172, compound

HRID 1818643Notes

Reaction equation

HRID 1818643 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:22][C:23]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=O.CCOCC>ClCCl>[F:22][C:23]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:24]=1[C:25]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 68297N-Phenyl-o-phenylenediamineHCID 5880812,4-Difluorobenzoyl chloride

Product 1

HCID 20826172HCID 20826172, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-phenyl-1,2-phenylenediamine (1.84 g, 10 mmol) and 40 ml of dichloromethane were charged in a 250 ml round bottle, 3 ml of triethylamine was added, and the mixture was cooled to 0° C. 2,4-Difluoro-benzoyl chloride (1.94 g, 11 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 precipitate. 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-phenyl-1H-benzoimidazole (yield=1.83 g, 60%).

Workup

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

Sources & evidence

ORD record
ord-c1301280758c4ea1b304b06d30c008a6
Source dataset
uspto-grants-2009_10
Patent number
US07601437B2

Reaction notes

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