Water → HCID 178506211, compound

HRID 1468132Notes

Reaction equation

HRID 1468132 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]([NH2:19])=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1.O.C(=O)(O)[O-].[Na+].[F:27][C:28]([F:36])([F:35])[C:29]([F:34])([F:33])[C:30](O)=O>>[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][CH:10]=2)=[CH:6][C:5]2[NH:19][C:30]([C:29]([F:34])([F:33])[C:28]([F:36])([F:35])[F:27])=[N:20][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 62356Pentafluoropropionic acidHCID 516892Sodium BicarbonateHCID 86699559HCID 86699559, compound

Product 1

HCID 178506211HCID 178506211, compoundYield 49.7%

Procedure

A solution of 4-chloro-5-[4-(trifluoromethyl)phenoxy]benzene-1,2-diamine (200 mg, 0.66 mmol) in pentafluoropropanoic acid (2 ml) was stirred overnight at 80° C. in an oil bath. The solution was poured into water (50 ml), adjusted pH to 8 with sodium bicarbonate (sat) 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 8% ethyl acetate in petroleum ether to produce 5-chloro-2-(pentafluoroethyl)-6-[4-(trifluoromethyl)phenoxy]-1H-1,3-benzodiazole as a white solid (141.7 g, 49.7%).

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 8% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-3d440ba4c3d4481d96b2a5ef2b7c2419
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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