Dichloromethane → HCID 67607839, compound

HRID 2405457Notes

Reaction equation

HRID 2405457 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[CH:6][CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.C(Cl)Cl>C1(C)C(C)=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:15]=[C:16]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 67891722HCID 67891722, compound

Product 1

HCID 67607839HCID 67607839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

2.1 g (5.7 mmol) of N-[2-(3-bromophenylamino)phenyl]benzamide was suspended in 30 mL of xylene. After the addition of 0.6 g (2.9 mmol) of p-toluenesulfonic acid monohydrate, the mixture was subjected to azeotropic dehydration under heat reflux for 3 hours. After allowing the reaction solution to cool, ethyl acetate, methylene chloride, and water were added to the reaction solution, and an insoluble component was removed by filtration. The organic phase was extracted from the mother filtrate, washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1-(3-bromophenyl)-2-phenyl-1H-benzimidazole.

Workup

  1. temperatureunder heat
  2. temperaturereflux for 3 hours
  3. temperatureto cool
  4. customan insoluble component was removed by filtration
  5. extractionThe organic phase was extracted from the mother filtrate
  6. washwashed with water
  7. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  8. customThe solvent was then evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ad7c013df0264650925c5a1de58d5b9d
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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