Heptafluorobutyric acid → HCID 178506101, compound

HRID 1468148Notes

Reaction equation

HRID 1468148 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:14]=[C:15]([NH2:21])[C:16]([NH2:20])=[CH:17][C:18]=1[Cl:19].[F:24][C:25]([F:36])([F:35])[C:26]([F:34])([F:33])[C:27]([F:32])([F:31])[C:28](O)=O>>[F:23][C:2]([F:22])([F:1])[C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:4]=1[C:13]1[C:18]([Cl:19])=[CH:17][C:16]2[N:20]=[C:28]([C:27]([F:31])([F:32])[C:26]([F:33])([F:34])[C:25]([F:36])([F:35])[F:24])[NH:21][C:15]=2[CH:14]=1

Participants

3

Reactant 2

HCID 9777Heptafluorobutyric acidHCID 86699571HCID 86699571, compound

Product 1

HCID 178506101HCID 178506101, compoundYield 31%

Procedure

A solution of 4-[2,4-bis(trifluoromethyl)phenyl]-5-chlorobenzene-1,2-diamine (300 mg, 0.85 mmol) in heptafluorobutanoic acid (20 ml) was stirred overnight at 80° C. in an oil bath and then quenched with water (100 ml). The pH value of the solution was adjusted to 8 with sodium carbonate and extracted with ethyl acetate (50 ml×3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by Pre-TLC with 10% ethyl acetate in petroleum ether to produce 6-[2,4-bis(trifluoromethyl)phenyl]-5-chloro-2-(heptafluoropropyl)-1H-1,3-benzodiazole as a pink solid (137.7 mg, 31%).

Workup

  1. customquenched with water (100 ml)
  2. extractionextracted with ethyl acetate (50 ml×3)
  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 Pre-TLC with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-8a7c0fed56f14af4a68a98569d65b6e8
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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