Heptafluorobutyric acid → HCID 178506102, compound

HRID 1468158Notes

Reaction equation

HRID 1468158 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]([NH2:19])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[Cl:18].[F:21][C:22]([F:33])([F:32])[C:23]([F:31])([F:30])[C:24]([F:29])([F:28])[C:25](O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][C:9]=2[Cl:18])=[CH:6][C:5]2[NH:19][C:25]([C:24]([F:28])([F:29])[C:23]([F:30])([F:31])[C:22]([F:33])([F:32])[F:21])=[N:20][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 9777Heptafluorobutyric acidHCID 10340Sodium CarbonateHCID 86699582HCID 86699582, compound

Product 1

HCID 178506102HCID 178506102, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-chloro-5-[2-chloro-4-(trifluoromethyl)phenyl]benzene-1,2-diamine (120 mg, 0.37 mmol), heptafluorobutanoic acid (5 ml) was stirred overnight at 80° C. in an oil bath. The solution was diluted with water (100 ml), adjusted to pH 7 with saturated aqueous sodium carbonate and extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 10% ethyl acetate in petroleum ether to produce 5-chloro-6-[2-chloro-4-(trifluoromethyl)phenyl]-2-(heptafluoropropyl)-1H-1,3-benzodiazole as a white solid (100.3 mg, 54%).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by a silica gel column with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-34d254850ce541649c427ce68f78f2f9
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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