Ammonium Chloride → HCID 20239564, compound

HRID 364654Notes

Reaction equation

HRID 364654 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([Li])[CH:6]=[CH:7][CH:8]=1.[CH2:12]([N:14]([CH2:28][CH3:29])[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:27])[CH2:25][CH3:26])=[CH:20][CH:19]=1)[CH3:13].[Cl-].[NH4+]>CCOCC>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[C:24]([CH2:25][CH3:26])([OH:27])[C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][N:14]([CH2:28][CH3:29])[CH2:12][CH3:13])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2099871-{4-[2-(diethylamino)ethoxy]phenyl}propan-1-oneHCID 178506715HCID 178506715, compound

Product 1

HCID 20239564HCID 20239564, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 250 ml. of a 0.4 molar solution of 3-trifluoromethylphenyl-lithium in ether a solution of 6.3 g. of 4'-[2-(diethylamino)-ethoxy]-propionphenone in 60 ml. of dry ether is added dropwise, under argon atmosphere, at -30° C., and the reaction mixture is stirred at room temperature for two hours. After cooling the reaction mixture is decomposed with a saturated, aqueous ammonium chloride solution, and the aqueous phase is extracted with ether. The ethereal phases are combined, washed to neutral with water and dried over anhydrous magnesium sulfate. Ether is distilled off under reduced pressure. The residue is chromatographed on a silica gel column with a 7:3 mixture of benzene and ethyl acetate. The solvent mixture is distilled in vacuo, and the residue is crystallized from n-hexane. 3.2 g. of the title compound are obtained, melting at 74° to 75° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionthe aqueous phase is extracted with ether
  3. washwashed to neutral with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationEther is distilled off under reduced pressure
  6. customThe residue is chromatographed on a silica gel column with a 7:3 mixture of benzene and ethyl acetate
  7. distillationThe solvent mixture is distilled in vacuo
  8. customthe residue is crystallized from n-hexane

Sources & evidence

ORD record
ord-159ccbfad3eb41e4b13669163b569c1d
Source dataset
uspto-grants-1986_08
Patent number
US04605672

Reaction notes

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