Heptafluorobutyric acid → HCID 178506100, compound

HRID 1468137Notes

Reaction equation

HRID 1468137 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:19])[C:5]([NH2:18])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:26][C:27]([F:38])([F:37])[C:28]([F:36])([F:35])[C:29]([F:34])([F:33])[C:30](O)=O>O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:6][C:5]2[NH:18][C:30]([C:29]([F:33])([F:34])[C:28]([F:35])([F:36])[C:27]([F:38])([F:37])[F:26])=[N:19][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 9777Heptafluorobutyric acidHCID 10340Sodium CarbonateHCID 86699564HCID 86699564, compound

Product 1

HCID 178506100HCID 178506100, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of 4-chloro-5-[4-(trifluoromethyl)phenyl]benzene-1,2-diamine (250 mg, 0.87 mmol) in heptafluorobutanoic acid (1.5 ml) was stirred overnight at 80° C. The result mixture was diluted with water (50 ml) and adjusted to pH 7 with saturated aqueous sodium carbonate. The resulting solution was extracted with ethyl acetate (3×50 ml), combined and dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was precipitated from dichloromethane (5 ml) to produce 5-chloro-2-(heptafluoropropyl)-6-[4-(trifluoromethyl)phenyl]-1H-1,3-benzodiazole as a white solid (194.8 mg, 48%).

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate (3×50 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. customwas precipitated from dichloromethane (5 ml)

Sources & evidence

ORD record
ord-5d89dc1e3b124c228a6af773705dcd0f
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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