Heptafluorobutyric acid → HCID 178506194, compound

HRID 1468153Notes

Reaction equation

HRID 1468153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]([NH2:19])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[C:15]([F:18])([F:17])[F:16].[F:21][C:22]([F:33])([F:32])[C:23]([F:31])([F:30])[C:24]([F:29])([F:28])[C:25](O)=O>>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[C:15]([F:17])([F:18])[F:16])=[CH:6][C:5]2[NH:19][C:25]([C:24]([F:28])([F:29])[C:23]([F:30])([F:31])[C:22]([F:33])([F:32])[F:21])=[N:20][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 9777Heptafluorobutyric acidHCID 866995774-Chloro-5-[4-chloro-2-(trifluoromethyl)phenyl]benzene-1,2-diamine

Product 1

HCID 178506194HCID 178506194, compoundYield 68%

Procedure

A solution of 4-chloro-5-[4-chloro-2-(trifluoromethyl)phenyl]benzene-1,2-diamine (100 mg, 0.31 mmol, 1.00 equiv) in heptafluorobutanoic acid (5 ml) was stirred overnight at 80° C. in an oil bath and then quenched with ice-water (30 ml). The pH value of the solution was adjusted to 8 with saturated aqueous 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 5-chloro-6-[4-chloro-2-(trifluoromethyl)phenyl]-2-(heptafluoropropyl)-1H-1,3-benzodiazole as a off-white solid (105.8 mg, 68%).

Workup

  1. customquenched with ice-water (30 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-b7a822fca7bc4c7a8da9b6cbff492794
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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