Hydrochloric Acid → HCID 178506328, compound

HRID 1468128Notes

Reaction equation

HRID 1468128 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH2:15])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.Cl.O.C(=O)(O)[O-].[Na+].[F:24][C:25]([F:33])([F:32])[C:26]([F:31])([F:30])[C:27](O)=O>>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)=[CH:6][C:5]2[NH:15][C:27]([C:26]([F:31])([F:30])[C:25]([F:33])([F:32])[F:24])=[N:16][C:4]=2[CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 62356Pentafluoropropionic acidHCID 516892Sodium BicarbonateHCID 86699539HCID 86699539, compound

Product 1

HCID 178506328HCID 178506328, compoundYield 40%

Conditions

Temperature
100 °C

Procedure

To a solution of 4-chloro-5-(4-chlorophenyl)benzene-1,2-diamine (100 mg, 0.40 mmol) in pentafluoropropanoic acid (5 ml) was added hydrogen chloride (conc) (1 ml). The resulting solution was stirred overnight at 100° C. and then poured into water (50 ml), adjusted pH value of the solution to 8 with sodium bicarbonate (sat). The resulting solution was extracted with ethyl acetate (3×30 ml), combined and dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column with 8% ethyl acetate in petroleum ether to produce 5-chloro-6-(4-chlorophenyl)-2-(pentafluoroethyl)-1H-1,3-benzodiazole as a white solid (60.8 mg, 40%).

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate (3×30 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. customwas purified by a silica gel column with 8% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-e9221d4f45784e539a2e2bd3d1e82058
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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