Heptafluorobutyric acid → HCID 178505492, compound

HRID 1468124Notes

Reaction equation

HRID 1468124 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH2:15])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.[F:17][C:18]([F:29])([F:28])[C:19]([F:27])([F:26])[C:20]([F:25])([F:24])[C:21](O)=O>>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)=[CH:6][C:5]2[NH:15][C:21]([C:20]([F:24])([F:25])[C:19]([F:26])([F:27])[C:18]([F:29])([F:28])[F:17])=[N:16][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 9777Heptafluorobutyric acidHCID 86699550HCID 86699550, compound

Product 1

HCID 178505492HCID 178505492, compoundYield 33%

Procedure

A solution of 4-chloro-5-(4-fluorophenyl)benzene-1,2-diamine (200 mg, 0.85 mmol) in heptafluorobutanoic acid (1.5 ml) was stirred overnight at 80° C. The reaction was then quenched by the addition of water (100 ml), adjusted to pH 7 with saturated aqueous sodium bicarbonate. The resulting solution was extracted with ethyl acetate (3×50 ml) and the organic layers were combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum to give a residue, which was purified by Pre-TLC with 10% ethyl acetate in petroleum ether to produce 5-chloro-6-(4-fluorophenyl)-2-(heptafluoropropyl)-1H-1,3-benzodiazole as a white solid (116.6 mg, 33%).

Workup

  1. customThe reaction was then quenched by the addition of water (100 ml)
  2. extractionThe resulting solution was extracted with ethyl acetate (3×50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customto give a residue, which
  7. customwas purified by Pre-TLC with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-d77f668d706440cbb7c4225f11cc7335
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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