Heptafluorobutyric acid → HCID 178506210, compound

HRID 1468133Notes

Reaction equation

HRID 1468133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]([NH2:19])=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1.[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(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][CH:10]=2)=[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

4

Reactant 2

HCID 9777Heptafluorobutyric acidHCID 86699559HCID 86699559, compound

Product 1

HCID 178506210HCID 178506210, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chloro-5-[4-(trifluoromethyl)phenoxy]benzene-1,2-diamine (200 mg, 0.66 mmol) in heptafluorobutanoic acid (3 ml) was stirred overnight at 80° C. in an oil bath. The solution was diluted with ethyl acetate (100 ml), washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by Pre-TLC with 10% ethyl acetate in petroleum ether to produce 5-chloro-2-(heptafluoropropyl)-6-[4-(trifluoromethyl)phenoxy]-1H-1,3-benzodiazole as a white solid (135.2 mg, 43%).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by Pre-TLC with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-7a6aa053e3fe45f2a1490d0b30908b46
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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