Hydroxyamine hydrochloride → HCID 59240453, compound

HRID 1673036Notes

Reaction equation

HRID 1673036 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13](=O)[CH2:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[N:10]=[C:9]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[C:4]([Cl:29])[CH:3]=1.Cl.[NH2:31]O>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]([C:16]([F:18])([F:19])[F:17])[O:20][N:31]=3)[N:10]=[C:9]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[C:4]([Cl:29])[CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 59240304HCID 59240304, compound

Product 1

HCID 59240453HCID 59240453, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 50 mL flask attached with condenser was added 1-(1-(4-bromo-2-chlorophenyl)-2-(2-chlorophenyl)-1H-imidazol-4-yl)-4,4,4-trifluorobutane-1,3-dione (138 mg, 273 μmol) and MeOH (12 mL). To the solution was added hydroxylamine-HCl (190 mg, 2.73 mmol). The reaction solution was allowed to stir at reflux for 1.5 h. The solution was concentrated in vacuo and the residue was taken into EtOAc and washed with aq. NaHCO3 (50 mL×2). The EtOAc phase was partitioned, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was chromatographed through a 12 g SiO2 column using a 100% hexane to 60% EtOAc gradient to yield 120 mg (86% yield) of title compound. MS (ESI) 508.3, 510.3 [M+H]+.

Workup

  1. customTo a 50 mL flask attached with condenser
  2. temperatureat reflux for 1.5 h
  3. concentrationThe solution was concentrated in vacuo
  4. washwashed with aq. NaHCO3 (50 mL×2)
  5. customThe EtOAc phase was partitioned
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was chromatographed through a 12 g SiO2 column

Sources & evidence

ORD record
ord-babf5f0f032340e2965fe8295b83f296
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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