1,3-dihydro-1-(2-hydroxy-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-2H-Benzimidazol-2-one → HCID 19001544, compound

HRID 2259636Notes

Reaction equation

HRID 2259636 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][C:15]=2[NH:14][C:13]1=[O:25].[N+:26]([O-])([O-:28])=[O:27].[K+]>S(=O)(=O)(O)O>[OH:1][C:2]1[C:7]([N+:26]([O-:28])=[O:27])=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[N:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:23])[F:22])=[CH:20][C:15]=2[NH:14][C:13]1=[O:25]

Participants

4

Reactant 2

HCID 45521,3-dihydro-1-(2-hydroxy-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-2H-Benzimidazol-2-oneHCID 24434Potassium Nitrate

Product 1

HCID 19001544HCID 19001544, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To an ice cooled solution of 1-(2-Hydroxy-5-trifluoromethylphenyl)-5-trifluoromethyl-1,3-dihydro-2H-benzimidazol-2-one (1.38 mmol, 0.50 g) in concentrated sulphuric acid (6 ml) is added an ice cooled solution of potassium nitrate (1.38 mmol, 0.14 g) in concentrated sulphuric acid (8 ml). The reaction mixture is allowed to reach room temperature and is poured into ice. The crude product is collected by filtration and subjected to column chromatography using methylenechloride+methanol (9+1 ) as eluent. The fractions containing the product are concentrated in vacuo yielding the title compound as slightly yellow crystals, M.p.>360° C.

Workup

  1. customto reach room temperature
  2. additionis poured into ice
  3. filtrationThe crude product is collected by filtration
  4. additionThe fractions containing the product
  5. concentrationare concentrated in vacuo

Sources & evidence

ORD record
ord-f8f99e8e4a884de7acf9ec9d75e079e3
Source dataset
uspto-grants-1995_12
Patent number
US05475015

Reaction notes

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