Trifluoroacetic acid → HCID 178506269, compound

HRID 1468113Notes

Reaction equation

HRID 1468113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:17])=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16].[F:19][C:20]([F:25])([F:24])[C:21](O)=O>Cl>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[CH:6][C:5]2[NH:17][C:21]([C:20]([F:25])([F:24])[F:19])=[N:18][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20337896HCID 20337896, compound

Product 1

HCID 178506269HCID 178506269, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-chloro-5-(2,4-dichlorophenoxy)benzene-1,2-diamine (100 mg, 0.33 mmol) in trifluoroacetic acid (5 ml) and hydrogen chloride (conc. 1 ml) was stirred overnight at 80° C. The reaction was then quenched water (100 ml), extracted with ethyl acetate (2×50 ml) and the organic layers combined. The resulting mixture was washed with saturated aqueous NaHCO3 (100 ml), dried over anhydrous sodium sulfate and concentrated under reduce pressure to give a residue, which was purified by a silica gel column with 5%˜10% ethyl acetate in petroleum ether to produce 5-chloro-6-(2,4-dichlorophenoxy)-2-(trifluoromethyl)-1H-1,3-benzodiazole as a white solid (82.4 mg, 66%).

Workup

  1. extractionquenched water (100 ml), extracted with ethyl acetate (2×50 ml)
  2. washThe resulting mixture was washed with saturated aqueous NaHCO3 (100 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas purified by a silica gel column with 5%˜10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-6265a51c23844d67b29c8f26c26add63
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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