Water → HCID 178505876, compound

HRID 1468119Notes

Reaction equation

HRID 1468119 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:37])([F:36])[C:27]([F:35])([F:34])[C:28]([F:33])([F:32])[C:29](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:29]([C:28]([F:32])([F:33])[C:27]([F:34])([F:35])[C:26]([F:37])([F:36])[F:25])=[N:18][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 9777Heptafluorobutyric acidHCID 516892Sodium BicarbonateHCID 86699544HCID 86699544, compound

Product 1

HCID 178505876HCID 178505876, compoundYield 21%

Procedure

A solution of 4-chloro-5-(2,4-difluorophenoxy)benzene-1,2-diamine (100 mg, 0.37 mmol) in heptafluorobutanoic acid (2 ml) was stirred overnight at 90° C. The mixture was poured into water (100 ml), adjusted pH value of the solution to 8 with sodium bicarbonate (solution) 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 10% ethyl acetate in petroleum ether to produce 5-chloro-6-(2,4-difluorophenoxy)-2-(heptafluoropropyl)-1H-1,3-benzodiazole as a pink solid (34.1 mg, 21%).

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 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-a8769266c4904eb0b95d21f739242dd3
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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