Imidazole → HCID 58641524, compound

HRID 2224074Notes

Reaction equation

HRID 2224074 reaction equation
[C:1]1([S:7]([C:10]2[CH:23]=[CH:22][C:13]3[N:14]([C:18](=[O:21])[CH2:19]Cl)[CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1.C(OCC)(=O)C>C(#N)C.[I-].[Na+]>[C:1]1([S:7]([C:10]2[CH:23]=[CH:22][C:13]3[N:14]([C:18](=[O:21])[CH2:19][N:30]4[CH:34]=[CH:33][N:32]=[CH:31]4)[CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 58641527HCID 58641527, compound

Product 1

HCID 58641524HCID 58641524, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-2-chloro-ethanone (0.216 g., 0.614 mmol) in 2 mL acetonitrile was added potassium carbonate (0.101 g., 0.737 mmol), imidazole (0.209 g., 3.07 mmol) and sodium iodide (2 mg, cat.), and the resulting suspension was refluxed for 2 hours. The reaction mixture was added to 100 mL ethyl acetate, and the inorganic components extracted three times with 50 mL water. The aqueous fraction was extracted twice with 50 mL ethyl acetate, and the combined organic fractions were dried over sodium sulfate and concentrated in vacuo. The crude solid was recrystallized from 3 mL dichloromethane to give 100 mg (42%) of 1-(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-2-imidazol-1-yl-ethanone as a white solid. MS: 385 (M+H)+.

Workup

  1. temperaturethe resulting suspension was refluxed for 2 hours
  2. extractionthe inorganic components extracted three times with 50 mL water
  3. extractionThe aqueous fraction was extracted twice with 50 mL ethyl acetate
  4. dry with materialthe combined organic fractions were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude solid was recrystallized from 3 mL dichloromethane

Sources & evidence

ORD record
ord-47d7c0409f1a4921a2d8b95b81be0585
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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