Proton sponge → HCID 72312846, compound

HRID 1161472Notes

Reaction equation

HRID 1161472 reaction equation
CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.F[B-](F)(F)F.C[O+:23]([CH3:25])[CH3:24].[CH3:26][O:27][C:28](=[O:59])[N:29]=[C:30]([S:57][CH3:58])[C:31]([C:45]1[CH:46]=[C:47]([O:55][CH3:56])[C:48]2[O:52][CH2:51]C(O)[C:49]=2[CH:54]=1)=[N:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[N:43]=[C:42]([CH3:44])[O:41][N:40]=2)=[CH:35][CH:34]=1.C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C>[CH3:26][O:27][C:28](=[O:59])[N:29]=[C:30]([S:57][CH3:58])[C:31]([C:45]1[CH:46]=[C:47]([O:55][CH3:56])[C:48]2[O:52][CH2:51][CH:24]([O:23][CH3:25])[C:49]=2[CH:54]=1)=[N:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[N:43]=[C:42]([CH3:44])[O:41][N:40]=2)=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 88675Proton spongeHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 72312803HCID 72312803, compound

Product 1

HCID 72312846HCID 72312846, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 201 mg of 1,8-bis(dimethylamino)naphthalene and 138 mg of trimethyloxonium tetrafluoroborate to a solution of 150 mg of {2-(3-hydroxy-7-methoxy-2,3-dihydrobenzofuran-5-yl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 3 ml of acetonitrile at 0° C., the mixture was stirred for 2 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, and extraction was performed with ethyl acetate. After washing the organic layer with water and saturated brine, it was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (80 mg) as a yellow oil.

Workup

  1. washAfter washing the organic layer with water and saturated brine, it
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-71f2001a6d11440399cded791e3f1b1b
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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