N-Phenyl-o-phenylenediamine → HCID 19353957, compound

HRID 1291951Notes

Reaction equation

HRID 1291951 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:15](Cl)(=O)[C:16]1[C:17]([O:22][CH3:23])=[CH:18][CH:19]=[CH:20][CH:21]=1>CN1CCCC1=O>[C:1]1([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=[C:15]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=[C:15]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 68297N-Phenyl-o-phenylenediamineHCID 889692-Methoxybenzoyl chloride

Product 2

HCID 19353957HCID 19353957, compoundHCID 13571111294212-05-2

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-phenyl-1,2-phenylenediamine (25 g, 0.136 mol) was dissolved in 100 ml N-methyl-2-pyrrolidinone (NMP) and o-anisoyl chloride (23.2 g, 0.136 mol) was then added to the solution at room temperature under nitrogen. The reaction mixture was stirred for 30 minutes at room temperature and then the temperature was increased to 220° C. for three hours during which time a white solid precipitated out of solution. After cooling, 150 ml of water was added to the reaction mixture and product was extracted with 300 ml of dichloromethane. The organic layer was washed with water and then dried with sodium sulfate. After removal of the solvents, the desired product o-(N-phenyl-2-benzimidazolyl) anisole was obtained.

Workup

  1. temperaturethe temperature was increased to 220° C. for three hours during which time a white solid
  2. customprecipitated out of solution
  3. temperatureAfter cooling
  4. addition150 ml of water was added to the reaction mixture and product
  5. extractionwas extracted with 300 ml of dichloromethane
  6. washThe organic layer was washed with water
  7. dry with materialdried with sodium sulfate
  8. customAfter removal of the solvents

Sources & evidence

ORD record
ord-c2dca32bed4b420a9f21f3eaef836bf7
Source dataset
uspto-grants-1998_05
Patent number
US05755999

Reaction notes

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