Hydrochloric Acid → HCID 178506234, compound

HRID 1009161

Reaction equation

HRID 1009161 reaction equation
CCO.Cl.[CH2:5]([NH:12]/[C:13](/[C:21]1[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:22]=1[OH:28])=[CH:14]\[C:15](=O)[C:16]([F:19])([F:18])[F:17])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O.N.CCOC(C)=O>[Br:27][C:25]1[CH:26]=[C:21]2[C:22](=[CH:23][CH:24]=1)[O:28][C:15]([C:16]([F:18])([F:19])[F:17])=[CH:14]/[C:13]/2=[N:12]/[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67304920(Z)-4-(benzylamino)-4-(5-bromo-2-hydroxyphenyl)-1,1,1-trifluorobut-3-en-2-one

Product 1

HCID 178506234HCID 178506234, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (ice bath) EtOH (96 ml) was bubbled through hydrogen chloride gas for 30 min. (Z)-4-(benzylamino)-4-(5-bromo-2-hydroxyphenyl)-1,1,1-trifluorobut-3-en-2-one (24.0 g, 60 mmol) was then added in one portion to this solution. The reaction was stirred at RT for 36 h. The resulted mixture was diluted with 900 ml of cool water, 28% aq NH3 (96 ml) was then added. The precipitate formed was filtered and washed with water to give a brown sticky solid. The solid was dissolved in EtOAc, washed with 1N HCl and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was crystallized from hexane to give the title compound as a brown solid. MS m/z: 382.

Workup

  1. additionwas then added in one portion to this solution
  2. additionwas then added
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customto give a brown sticky solid
  7. washwashed with 1N HCl and brine
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-14124da969ab465ab56f57c7f3686a9b
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Linked notes

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