Heptafluorobutyric acid → HCID 178506212, compound

HRID 1468144Notes

Reaction equation

HRID 1468144 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:34])([F:33])[C:24]([F:32])([F:31])[C:25](F)(F)C(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:32])([F:31])[C:23]([F:34])([F:33])[F:22])=[N:21][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 9777Heptafluorobutyric acidHCID 86699569HCID 86699569, compound

Product 1

HCID 178506212HCID 178506212, compoundYield 54%

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzene-1,2-diamine (50 mg, 0.15 mmol) was added heptafluorobutanoic acid (3 ml). The resulting solution was stirred overnight at 80° C. and quenched with the addition of water (100 ml). The pH value of the solution was adjusted to 8 with potassium carbonate, extracted with ethyl acetate (3×50 ml), organic layers combined, 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 light yellow solid (41.2 mg, 54%).

Workup

  1. customquenched with the addition of water (100 ml)
  2. extractionextracted with ethyl acetate (3×50 ml), organic layers
  3. dry with materialdried 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-6c3364be4188495d95588b3432c5731a
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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