(Diethylamino)sulfur trifluoride → HCID 59398570, compound

HRID 2070040Notes

Reaction equation

HRID 2070040 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17]O)=[C:10]([C:19]([F:22])([F:21])[F:20])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:30])CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][F:30])=[C:10]([C:19]([F:22])([F:21])[F:20])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59398558HCID 59398558, compound

Product 1

HCID 59398570HCID 59398570, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-(4-Hydroxybutyl)-3-trifluoromethylphenyl]carbamic acid tert-butyl ester (190 mg, 0.57 mmol) was dissolved in DCM (2 mL), and DAST (153 mg, 0.95 mmol) was added thereto. The resulting mixture was stirred at room temperature for 2 hours. The reaction solution was quenched with a saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=5:1) to give [4-(4-fluorobutyl)-3-trifluoromethylphenyl]carbamic acid tert-butyl ester (96 mg, 50%) as a light-yellow oil.

Workup

  1. customThe reaction solution was quenched with a saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-3d678da80d7a4fbb89a2fcddb4ea71c9
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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