Pentafluoropropionic acid → HCID 178506104, compound

HRID 1468147Notes

Reaction equation

HRID 1468147 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:33])([F:32])[C:26]([F:31])([F:30])[C:27](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:27]([C:26]([F:31])([F:30])[C:25]([F:33])([F:32])[F:24])[NH:21][C:15]=2[CH:14]=1

Participants

3

Reactant 2

HCID 62356Pentafluoropropionic acidHCID 86699571HCID 86699571, compound

Product 1

HCID 178506104HCID 178506104, compound

Procedure

A solution of 4-[2,4-bis(trifluoromethyl)phenyl]-5-chlorobenzene-1,2-diamine (300 mg, crude) in pentafluoropropanoic acid (20 ml) was stirred overnight at 80° C. in an oil bath and then quenched with ice-water (50 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 layer was 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-(pentafluoroethyl)-1H-1,3-benzodiazole as a off-white solid (76.1 mg).

Workup

  1. customquenched with ice-water (50 ml)
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. dry with materialThe combined organic layer was 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-4dfe81d49d3241078de53cad53f08b6a
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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