Pentafluoropropionic acid → HCID 178505493, compound

HRID 1468123Notes

Reaction equation

HRID 1468123 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:26])([F:25])[C:19]([F:24])([F:23])[C:20](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:20]([C:19]([F:24])([F:23])[C:18]([F:26])([F:25])[F:17])=[N:16][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 62356Pentafluoropropionic acidHCID 86699550HCID 86699550, compound

Product 1

HCID 178505493HCID 178505493, compoundYield 43%

Procedure

A solution of 4-chloro-5-(4-fluorophenyl)benzene-1,2-diamine (200 mg, 0.85 mmol) in pentafluoropropanoic acid (2 ml) was stirred for 10 h at 80° C. The reaction was then quenched by the addition of water (100 ml), pH adjusted to 7 with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×100 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure 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-(pentafluoroethyl)-1H-1,3-benzodiazole as a white solid (132.4 mg, 43%).

Workup

  1. customThe reaction was then quenched by the addition of water (100 ml)
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue, which
  6. customwas purified by Pre-TLC with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-8eb096ddc5bc4489a13dc00f314b73be
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

Loading…