Hydrochloric Acid → HCID 57820108, compound

HRID 1714171Notes

Reaction equation

HRID 1714171 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:38])[N:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)C(C3C=CC=CC=3)[N:10]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[C:9]2=[O:37])=[CH:4][CH:3]=1.Cl>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)([CH3:38])[C:9]([NH:10][C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:31][CH:32]=2)=[O:37])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57819944HCID 57819944, compound

Product 1

HCID 57820108HCID 57820108, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 5-(4-bromo-phenyl)-5-methyl-1-(2-morpholin-4-yl-ethyl)-2-phenyl-3-(4-trifluoromethyl-phenyl)-imidazolidin-4-one (1.0 g, 1.7 mmol) was stirred vigorously in a solution of dichloromethane:conc. HCl (10 mL: 50 mL, v:v) overnight at 80 degrees Celcius. The resulting mixture was cooled to room temperature and the aqueous portion was extracted with dichloromethane. The aqueous portion was then basified to pH 11 with aqueous NaOH. The aqueous layer was then extracted with dichloromethane, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with dichloromethane:methanol gradient (500:1 to 100:1, v/v) to afford the product as a pale yellow solid (233 mg, 27%). MS: calc'd 500 (MH+), exp 500 (MH+).

Workup

  1. customat 80 degrees
  2. extractionthe aqueous portion was extracted with dichloromethane
  3. extractionThe aqueous layer was then extracted with dichloromethane
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash column chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-5e2bdbde6bcd456b8a56a44e1e05ac20
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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