Sodium Hydroxide → HCID 13730384, compound

HRID 978040Notes

Reaction equation

HRID 978040 reaction equation
[Cl:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH:24]([O-])([O-])OCC.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:13][CH:12]=3)[CH:24]=[N:5][C:4]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 13730383HCID 13730383, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 13730384HCID 13730384, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-chloro-2-(4-phenoxybenzylamino)aniline (0.300 g) and ethyl ortho-formate (0.178 g) was heated at 120° to 130° C. for 5 hours while stirring and then cooled to room temperature. Toluene (100 ml) and a 5% sodium hydroxide solution (50 ml) were added thereto, followed by stirring for 10 minutes. The toluene layer was separated and washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove toluene. The residue was purified by silica gel column chromatography to give 7-chloro-1-(4-phenoxybenzyl)benzimidazole (0.239 g) as a colorless liquid. nD28.5 1.6362.

Workup

  1. temperaturewas heated at 120° to 130° C. for 5 hours
  2. stirringby stirring for 10 minutes
  3. customThe toluene layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove toluene
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40f5b96dd5254e17bc2bb1de21a9c7f7
Source dataset
uspto-grants-1987_05
Patent number
US04663339

Reaction notes

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