HCID 21555860, compound → HCID 66914820, compound

HRID 2104600Notes

Reaction equation

HRID 2104600 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[CH2:9][CH:10]=O.[NH2:13][C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:15]=1[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O>CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:9]1[CH:10]=[N:13][C:14]2[C:15]([C:24]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:16][CH:17]=[CH:18][C:19]=2[C:20]([F:23])([F:22])[F:21])=[O:12]

Participants

4

Reactant 2

HCID 21555860HCID 21555860, compoundHCID 431147113-(2-Fluorophenyl)-3-oxopropanal

Product 1

HCID 66914820HCID 66914820, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-(2-Fluorophenyl)-3-oxopropionaldehyde (0.451 g, 2.70 mmol) and [2-amino-3-(trifluoromethyl)phenyl](phenyl)methanone (0.119 g, 0.448 mmol) in AcOH (5 mL) is treated with 0.1 mL of 1:20H2SO4/AcOH solution and heated at reflux for 20 min. The cooled reaction is quenched with water and extracted with ethyl acetate twice. The combined organic layers are washed with saturated aq sodium bicarbonate and dried over MgSO4. The product is purified by chromatography (5:95 ethyl acetate:hexane) to afford the title compound as a yellow solid (0.162 g, 91.5%). MS (ESI) m/z 396.1009; HRMS: calcd for C23H13F4NO+H, 396.10115; found (ESI, [M+H]+), 396.1009.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 min
  3. customThe cooled reaction
  4. customis quenched with water
  5. extractionextracted with ethyl acetate twice
  6. washThe combined organic layers are washed with saturated aq sodium bicarbonate
  7. dry with materialdried over MgSO4
  8. customThe product is purified by chromatography (5:95 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-8a6dac3675ae45ac9e455e2f405bf18d
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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