Water → HCID 178505875, compound

HRID 1468127Notes

Reaction equation

HRID 1468127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]([NH2:16])=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.O.C(=O)(O)[O-].[Na+].[F:24][C:25]([F:36])([F:35])[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:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)=[CH:6][C:5]2[NH:16][C:28]([C:27]([F:31])([F:32])[C:26]([F:33])([F:34])[C:25]([F:36])([F:35])[F:24])=[N:17][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 9777Heptafluorobutyric acidHCID 516892Sodium BicarbonateHCID 86699555HCID 86699555, compound

Product 1

HCID 178505875HCID 178505875, compoundYield 2%

Procedure

A solution of 4-chloro-5-(4-fluorophenoxy)benzene-1,2-diamine (400 mg, 1.58 mmol) in heptafluorobutanoic acid (3 ml) was stirred overnight at 110° C. in an oil bath. The solution was poured into water (150 ml), adjusted pH to 8 with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×100 ml). The combined organic layers were 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-(4-fluorophenoxy)-2-(heptafluoropropyl)-1H-1,3-benzodiazole as a off-white solid (12.0 mg, 2%).

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. concentrationThe combined organic layers were concentrated under vacuum
  3. customto give a residue, which
  4. customwas purified by a silica gel column with 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-5eb8dbf6214c428e85fb0c3afe1cdf12
Source dataset
uspto-grants-2015_04
Patent number
US09000187B2

Reaction notes

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