Morpholine → 2-(1,3-dihydrobenzimidazol-2-ylidene)-1-(3-fluorophenyl)ethanone

HRID 2423229Notes

Reaction equation

HRID 2423229 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH3:11][C:12]1[NH:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1.C(N(CC)CC)C.N1CCOCC1>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH:11]=[C:12]2[NH:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[NH:13]2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 119842-MethylbenzimidazoleHCID 743763-Fluorobenzoyl chloride

Product 1

HCID 1785203792-(1,3-dihydrobenzimidazol-2-ylidene)-1-(3-fluorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Fluorobenzoyl chloride was added to a mixture of 2-methylbenzimidazole, triethylamine and dioxane, followed by heating under reflux for 3 hours and cooling to room temperature. Morpholine was added, followed by stirring under heat at 70° C. for 1 hour and work-up to obtain 1-(3-fluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)ethanone.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. temperatureunder heat at 70° C. for 1 hour

Sources & evidence

ORD record
ord-9932b0cee82643d9b83a981257901cbb
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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