2-Chloroimidazoline sulfate → HCID 9926737, compound

HRID 2228443Notes

Reaction equation

HRID 2228443 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.S(O)(O)(=O)=O.Cl[C:25]1[NH:26][CH2:27][CH2:28][N:29]=1>CC(O)C.C(OCC)(=O)C>[NH:29]1[CH2:28][CH2:27][N:26]=[C:25]1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 125033982-Chloroimidazoline sulfateHCID 18469984HCID 18469984, compound

Product 1

HCID 9926737HCID 9926737, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(4-aminophenyl)-1-(4-fluorophenyl)propan-1-one (1.17 g, 4.81 mmol) and 2-chloro-4,5-dihydro-1H-imidazole sulfate (1.95 g, 9.62 mmol) (prepared according to the procedure described in Trani, A and Bellasio, E., J. Het. Chem. 1974, 11, 257) in 2-propanol (20 mL) was heated under reflux for 15 minutes. The reaction mixture was cooled and diluted with ethyl acetate (150 mL) and washed with 5% sodium hydroxide solution, water, and brine. The organic layer was separated and dried with potassium carbonate, and evaporated in vacuo. Purification by silica gel chromatography, eluting with 10% methanol/dichloromethane containing 1% ammonium hydroxide, gave 3-[4-(4,5-dihydro-1H-imidazol-2-ylamino)phenyl]-1-(4-fluorophenyl)propan-1-one as an oil (1.01 g, 76.5%). The oil was converted to the hydrochloride salt, m.p. 190.2-190.8° C. Analysis for C18H19CIFN3O.0.2H20: Calcd.: C, 61.52; H, 5.56, N, 11.96. Found: C, 61.40; H, 5.47; N, 11.97.

Workup

  1. customprepared
  2. temperatureunder reflux for 15 minutes
  3. temperatureThe reaction mixture was cooled
  4. washwashed with 5% sodium hydroxide solution, water, and brine
  5. customThe organic layer was separated
  6. dry with materialdried with potassium carbonate
  7. customevaporated in vacuo
  8. customPurification by silica gel chromatography
  9. washeluting with 10% methanol/dichloromethane containing 1% ammonium hydroxide

Sources & evidence

ORD record
ord-e02508aa602d485195b912fc69e585b4
Source dataset
uspto-grants-2002_07
Patent number
US06417186B1

Reaction notes

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