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

HRID 1509468Notes

Reaction equation

HRID 1509468 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).

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-cd2574623f394195a7320f8347bd0566
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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