HCID 12261659, compound → HCID 22717685, compound

HRID 1582559Notes

Reaction equation

HRID 1582559 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[O:5][N:4]=[C:3]1[O:8]CC1C=CC=CC=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH:27]([CH3:29])[CH3:28])[C:24](Cl)=[O:25])=[CH:19][CH:18]=1>C(#N)C>[F:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]([CH:27]([CH3:29])[CH3:28])[C:24]([N:4]2[C:3](=[O:8])[N:2]([CH3:1])[C:6](=[O:7])[O:5]2)=[O:25])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 12261659HCID 12261659, compoundHCID 22717692HCID 22717692, compound

Product 1

HCID 22717685HCID 22717685, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 50 mL round bottom flask equipped with a thermometer, a stirrer and a nitrogen inlet was charged with 4-methyl-3-(phenylmethoxy)-1,2,4-oxadiazol-5(4H)-one (0.55 g, 2.66 mmol), (4-fluorophenyl)(1-methylethyl)carbamic chloride (0.581 g, 2.7 mmol), N,N′-dimethylaminopyridine (0.329 g, 2.7 mmol) and acetonitrile (10 mL). The reaction mixture was heated to reflux 2 h, and allowed to cool to room temperature. The entire mixture was flash chromatographed (silica gel, 9: 1, then 8:2 hexane-ethyl acetate) to provide 0.6 g (76%) of the title compound as a white solid melting at 135-136° C.

Workup

  1. customA 50 mL round bottom flask equipped with a thermometer, a stirrer and a nitrogen inlet
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux 2 h
  4. customchromatographed (silica gel, 9: 1

Sources & evidence

ORD record
ord-f8bb94a1be874991a5bbe08d566d8224
Source dataset
uspto-grants-2004_05
Patent number
US06737383B1

Reaction notes

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