Pentafluoropropionic acid → HCID 178506329, compound

HRID 1468114Notes

Reaction equation

HRID 1468114 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:17])=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16].[F:19][C:20]([F:28])([F:27])[C:21]([F:26])([F:25])[C:22](O)=O>>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[CH:6][C:5]2[NH:17][C:22]([C:21]([F:26])([F:25])[C:20]([F:28])([F:27])[F:19])=[N:18][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 62356Pentafluoropropionic acidHCID 20337896HCID 20337896, compound

Product 1

HCID 178506329HCID 178506329, compoundYield 15%

Procedure

A solution of 4-chloro-5-(2,4-dichlorophenoxy)benzene-1,2-diamine (100 mg, 0.33 mmol) in pentafluoropropanoic acid (5 ml) was stirred overnight at 80° C. in an oil bath. The reaction was then quenched by the addition of water (20 ml), adjusted to pH 7 with aqueous sodium bicarbonate and extracted with ethyl acetate (2×50 ml). The combined organic layers were dried over anhydrous magnesium sulfate and 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-(2,4-dichlorophenoxy)-2-(pentafluoroethyl)-1H-1,3-benzodiazole as a white solid (21.4 mg, 15%).

Workup

  1. customThe reaction was then quenched by the addition of water (20 ml)
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue which
  6. customwas purified by Pre-TLC with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-682d42a7438841f1adfa3599dc478f80
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

Loading…