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

HRID 1184139Notes

Reaction equation

HRID 1184139 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:4]=1.[Cl:17][C:18]([Cl:24])([Cl:23])[C:19](=N)OC>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]2[N:7]=[C:19]([C:18]([Cl:24])([Cl:23])[Cl:17])[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 58355599HCID 58355599, compound

Product 1

HCID 583557496-methoxy-1-(4-methoxybutyl)-2-(trichloromethyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methoxy-2-(4-methoxybutylamino)aniline (2.50 g) was dissolved in acetic acid (30 ml), methyl 2,2,2-trichloroethanimidate (1.62 ml) was added, and the mixture was stirred for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with diisopropyl ether, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the object product (1.75 g). MS (ESI+, m/e) 351 (M+1)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with diisopropyl ether
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8eeb25dcf354a3d8635b75986e51f7d
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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