Sodium Hydroxide → HCID 14800483, compound

HRID 704328Notes

Reaction equation

HRID 704328 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:3]=1[NH2:4].[C:29]([O-])([O-])(OCC)[CH3:30].[OH-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]2[N:4]=[C:29]([CH3:30])[N:9]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:26])=[O:27])=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14800482HCID 14800482, compoundHCID 86598186Ethyl ortho-acetate

Product 1

HCID 14800483HCID 14800483, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 2-fluoro-6-[4-(4-methylsulfonyloxyphenoxy)benzylamino]aniline (300 mg) and ethyl ortho-acetate (181 mg) was heated at 150° to 160° C. for 24 hours while stirring. The reaction mixture was cooled to room temperature, toluene (100 ml) and a 5% sodium hydroxide solution (50 ml) were added thereto, and the resultant mixture was stirred for 10 minutes The toluene layer was separated, washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to eliminate toluene. The residue was purified by silica gel column chromatography to give 4-fluoro-1-[4-(4-methylsulfonyloxyphenoxy)benzyl]-2-methylbenzimidazole (243 mg) as white crystals m.p., 48°-56° C.

Workup

  1. temperaturewas heated at 150° to 160° C. for 24 hours
  2. customwas separated
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ca76c696c0bd4142a38058b0c5ec4b60
Source dataset
uspto-grants-1991_01
Patent number
US04987145

Reaction notes

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