Pentafluoropropionic acid → HCID 178506212, compound

HRID 1468143Notes

Reaction equation

HRID 1468143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:21])[C:5]([NH2:20])=[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][C:10]=1[Cl:19].[F:22][C:23]([F:31])([F:30])[C:24]([F:29])([F:28])[C:25](O)=O>>[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][C:10]=2[Cl:19])=[CH:6][C:5]2[NH:20][C:25]([C:24]([F:29])([F:28])[C:23]([F:31])([F:30])[F:22])=[N:21][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 62356Pentafluoropropionic acidHCID 86699569HCID 86699569, compound

Product 1

HCID 178506212HCID 178506212, compoundYield 55%

Procedure

A solution of 4-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzene-1,2-diamine (50 mg, 0.15 mmol) in pentafluoropropanoic acid (3 ml) was stirred overnight at 80° C. The reaction was then quenched by the addition of water (100 ml), pH value adjusted to 8 with potassium carbonate and extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by Prep-HPLC to produce 5-chloro-6-[2-chloro-4-(trifluoromethyl)phenoxy]-2-(pentafluoroethyl)-1H-1,3-benzodiazole as a pink solid (38 mg, 55%).

Workup

  1. customThe reaction was then quenched by the addition of water (100 ml), pH value
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by Prep-HPLC

Sources & evidence

ORD record
ord-848d4b7ed6d4465eabc081b36e76015d
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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