(Diethylamino)sulfur trifluoride → HCID 68585577, compound

HRID 17603Notes

Reaction equation

HRID 17603 reaction equation
C(N(S(F)(F)[F:7])CC)C.[F:10][C:11]1[C:12]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:13]([CH3:26])[C:14]([C:24]#[N:25])=[C:15]2[C:19]=1[O:18][C:17]([C:20](O)([CH3:22])[CH3:21])=[N:16]2.C(=O)([O-])O.[Na+]>ClCCl>[F:10][C:11]1[C:12]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:13]([CH3:26])[C:14]([C:24]#[N:25])=[C:15]2[C:19]=1[O:18][C:17]([C:20]([F:7])([CH3:22])[CH3:21])=[N:16]2

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 685849927-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 68585577HCID 68585577, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, diethylaminosulfur trifluoride (293 μl, 2.24 mmol) was dropwise added at 0° C. to a dichloromethane (5 ml) solution of 7-fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-112) (139 mg, 448 μmol), followed by stirring at room temperature for 14 hours. At 0° C., an aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, then the mixture liquid was extracted with chloroform. Next, the combined organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=5:1, v/v) to obtain the entitled compound (134 mg, 96%) as a pale yellow solid.

Workup

  1. extractionthe mixture liquid was extracted with chloroform
  2. dry with materialNext, the combined organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-71a70f4191f54f96bfb9d88773bafb2e
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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