Dimethylformamide → HCID 66612203, compound

HRID 2390483Notes

Reaction equation

HRID 2390483 reaction equation
[C:1]([NH:5][C:6]1[C:7]([NH2:16])=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:19][N:20]([CH3:23])C=O>>[C:1]([N:5]1[C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:14])([F:15])[F:13])=[CH:8][C:7]=2[N:16]=[C:4]1[C:1]1[CH:3]=[CH:23][N:20]=[CH:19][CH:2]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 18509812HCID 18509812, compound

Product 1

HCID 66612203HCID 66612203, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 0.47 g of N1-tert-butyl-4-trifluoromethylbenzene-1,2-diamine, 0.51 g of isonicotinealdehyde-bisulfite adduct and 5 ml of N,N-dimethylformamide was stirred for 10 minutes at 150° C. The reaction mixture was ice-cooled, then, a 10% sodium hydroxide aqueous solution was poured, and the mixture was extracted with methyl tert-butyl ether. The organic layer was washed with water, dried over sodium sulfate, then, concentrated under reduced pressure to obtain a solid residue. The residue was washed with hexane, to obtain 0.26 g of 1-tert-butyl-2-(pyridin-4-yl)-5-trifluoromethyl-1H-benzimidazole (hereinafter, referred to as present active compound 220).

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with methyl tert-butyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a solid residue
  7. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-e48aa315fbb84228bb628a70aeeffe84
Source dataset
uspto-grants-2012_09
Patent number
US08273764B2

Reaction notes

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