Trifluoroacetic acid → 7-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazol-5-ol

HRID 1846498Notes

Reaction equation

HRID 1846498 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([CH3:9])[C:7]=1[NH2:8].[F:11][C:12]([F:17])([F:16])[C:13](O)=O.[OH-].[Na+]>>[CH3:9][C:6]1[C:7]2[NH:8][C:13]([C:12]([F:17])([F:16])[F:11])=[N:1][C:2]=2[CH:3]=[C:4]([OH:10])[CH:5]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 199076443,4-Diamino-5-methylphenol

Product 1

HCID 1784289667-methyl-2-(trifluoromethyl)-1H-benzo[d]imidazol-5-ol

Procedure

0.20 g (1.45 mmol) 3,4-diamino-5-methylphenol were stirred together with 1 mL (13.07 mmol) trifluoroacetic acid for 1 h at 100° C. The reaction mixture was cooled and purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with an aqueous 1M NaOH solution and extracted with ethyl acetate. The organic phase was evaporated down i.vac.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompurified by chromatography
  3. additionThe fractions containing product
  4. customevaporated down i.vac
  5. customto leave the aqueous residue
  6. extractionextracted with ethyl acetate
  7. customThe organic phase was evaporated down i.vac

Sources & evidence

ORD record
ord-3107e7f2a4a94f1ca9acd17073e0c509
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

Loading…