Methyl iodide → HCID 22717684, compound

HRID 1582560Notes

Reaction equation

HRID 1582560 reaction equation
C1(C[O:8][C:9]2[NH:13][C:12](=[O:14])[O:11][N:10]=2)C=CC=CC=1.I[CH3:16].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH:28]([CH3:30])[CH3:29])[C:25](Cl)=[O:26])=[CH:20][CH:19]=1>C(#N)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH:28]([CH3:30])[CH3:29])[C:25]([N:10]2[C:9](=[O:8])[N:13]([CH3:16])[C:12](=[O:14])[O:11]2)=[O:26])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14857249HCID 14857249, compoundHCID 13574419151991-60-7

Product 1

HCID 22717684HCID 22717684, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 50 mL round bottom flask, equipped with a thermometer, a stirrer and nitrogen inlet was charged with 3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one (0.5 g, 2.6 mmol), 1,8-diazabicyclo[5.4.0]unded-7-ene (0.5 g, 3.28 mmol), iodomethane (0.5 g, 3.54 mmol) and acetonitrile (5 mL). The mixture was stirred at room temperature for 18 h. To the mixture was added (4-chlorophenyl)(1-methylethyl)carbamic chloride (0.7 g, 3 mmol) and N,N′-dimethylamino-pyridine (0.367 g, 3 mmol), and the resulting mixture was heated to reflux for 2 h. It was then cooled to room temperature and flash chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide 150 mg (18%) of the title compound as a white solid melting at 121-123° C.

Workup

  1. customA 50 mL round bottom flask, equipped with a thermometer, a stirrer and nitrogen inlet
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 2 h
  4. temperatureIt was then cooled to room temperature
  5. customflash chromatographed (silica gel, 9:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5de2768c49ba42cfada06cff1f38f0cd
Source dataset
uspto-grants-2004_05
Patent number
US06737383B1

Reaction notes

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