Water → HCID 178505877, compound

HRID 1468118Notes

Reaction equation

HRID 1468118 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]([F:15])=[CH:11][C:10]=1[F:16].O.C(=O)(O)[O-].[Na+].[F:25][C:26]([F:34])([F:33])[C:27]([F:32])([F:31])[C:28](O)=O>>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[CH:6][C:5]2[NH:17][C:28]([C:27]([F:32])([F:31])[C:26]([F:34])([F:33])[F:25])=[N:18][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 62356Pentafluoropropionic acidHCID 516892Sodium BicarbonateHCID 86699544HCID 86699544, compound

Product 1

HCID 178505877HCID 178505877, compoundYield 16%

Procedure

A solution of 4-chloro-5-(2,4-difluorophenoxy)benzene-1,2-diamine (100 mg, 0.37 mmol) in pentafluoropropanoic acid (2 ml) was stirred overnight at 80° C. Then the mixture was poured into water (100 ml), adjusted pH to 7 with aqueous sodium bicarbonate and extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column with 5% ethyl acetate in petroleum ether to produce 5-chloro-6-(2,4-difluorophenoxy)-2-(pentafluoroethyl)-1H-1,3-benzodiazole as a white solid (24 mg, 16%).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. customwas purified by a silica gel column with 5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0e5793eb7ea44d9dabd514dc1afd71f8
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

Loading…