Water → HCID 178520378, compound

HRID 658091Notes

Reaction equation

HRID 658091 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].O.N1CCOCC1>COCCOCCOC.CO>[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](=[O:15])[CH:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[NH:3]1

Participants

7

Reactant 4

HCID 962Water2×HCID 8083MorpholineHCID 119842-MethylbenzimidazoleHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 178520378HCID 178520378, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8150DiglymeSolvent

Conditions

Temperature
100 °C

Procedure

A 4.0 g portion of 2-methyl-1H-benzimidazole and 13.9 ml of TEA were dissolved in 40 ml of Diglyme, and 17.5 g of 2-chlorobenzoic acid chloride was added dropwise thereto. The reaction mixture was stirred at 100° C. for 3 hours. After cooling to room temperature, the reaction mixture was mixed with water, extracted with chloroform, dried with anhydrous sodium sulfate and then concentrated, thereby obtaining an orange oily substance. This was dissolved in 60 ml of methanol, mixed with 7.9 ml of morpholine and then heated under reflux for 3.5 hours. The reaction mixture was cooled to room temperature, mixed with water and then stirred for 1 hour. The thus formed precipitate was collected by filtration, washed with cool water and then dried to obtain 6.1 g (75%) of 1-(2-chlorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)ethanone (Reference Example 1-2) as pale yellow powdery crystals. ES+: 271

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with chloroform
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customobtaining an orange oily substance
  6. temperatureheated
  7. temperatureunder reflux for 3.5 hours
  8. temperatureThe reaction mixture was cooled to room temperature
  9. stirringstirred for 1 hour
  10. filtrationThe thus formed precipitate was collected by filtration
  11. washwashed with cool water
  12. customdried

Sources & evidence

ORD record
ord-b5608c657793466186884d7a756cbb77
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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