Methyl 2,2,2-trichloroacetimidate → 6-fluoro-1-(4-methoxybutyl)-2-(trichloromethyl)-1H-benzimidazole

HRID 2168900Notes

Reaction equation

HRID 2168900 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:3]=1.[Cl:16][C:17]([Cl:23])([Cl:22])[C:18](=N)OC>C(O)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]2[N:6]=[C:18]([C:17]([Cl:23])([Cl:22])[Cl:16])[N:9]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 583555474-Fluoro-2-(4-methoxybutylamino)aniline

Product 1

HCID 583553976-fluoro-1-(4-methoxybutyl)-2-(trichloromethyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Fluoro-2-(4-methoxybutylamino)aniline (4.28 g) was dissolved in acetic acid (100 ml), methyl 2,2,2-trichloroethanimidate (2.49 ml) was added dropwise, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was azeotroped with toluene. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (6.53 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was azeotroped with toluene
  3. washa fraction eluted with ethyl acetate
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ee3c0a9a0f3437f8668539977027340
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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