Hydrochloric Acid → HCID 67199697, compound

HRID 1948719Notes

Reaction equation

HRID 1948719 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[F:9][C:10]([F:23])([F:22])[C:11]1[CH:12]=[C:13]([C:17](=O)[C:18](=O)[CH3:19])[CH:14]=[CH:15][CH:16]=1.Cl>O>[CH3:19][C:18]1[C:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:10]([F:9])([F:22])[F:23])[CH:12]=2)=[N:8][C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7243O-PhenylenediamineHCID 27776781-[3-(trifluoromethyl)phenyl]propane-1,2-dione

Product 1

HCID 67199697HCID 67199697, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1,2-phenylenediamine (1.00 g, 9.25 mmol) and 1-[3-(trifluoromethyl)phenyl]propane-1,2-dione (2.00 g, 9.25 mmol) in water (80 mL) was heated at 60° C. overnight, then for 5 h with vigorous stirring. The reaction mixture was allowed to cool to r.t. then acidified with 2N HCl (ca 20 mL) and extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was triturated with heptane to give the title compound (1.44 g, 54%) as a cream-coloured solid. δH (CDCl3) 8.05-8.16 (m, 2H), 7.96 (s, 1H), 7.85-7.90 (m, 1H), 7.72-7.82 (m, 3H), 7.64-7.71 (m, 1H), 2.79 (s, 3H). LCMS (ES+) 289.3 (M+H)+, RT 4.21 minutes (Method 3).

Workup

  1. temperatureto cool to r.t.
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with heptane

Sources & evidence

ORD record
ord-16cdae4321d84f418651b33d63c88703
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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