(Diethylamino)sulfur trifluoride → HCID 59398561, compound

HRID 2070036Notes

Reaction equation

HRID 2070036 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18]O)=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:31])CC>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][F:31])=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59398581HCID 59398581, compound

Product 1

HCID 59398561HCID 59398561, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-(2-Hydroxyethyl)-3-(trifluoromethyl)phenyl]carbamic acid benzyl ester (428 mg, 1.26 mmol) was dissolved in DCM (4 mL), and DAST (339 mL, 2.10 mmol) was added thereto. The resulting mixture was stirred for about 3 hours. The reaction solution was quenched with a saturated sodium bicarbonate solution, and then DCM (20 mL) was added thereto. The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=5:1) to give [4-(2-fluoroethyl)-3-(trifluoromethyl)phenyl]carbamic acid benzyl ester (194 mg, 45%) as a yellow oil.

Workup

  1. customThe reaction solution was quenched with a saturated sodium bicarbonate solution
  2. additionDCM (20 mL) was added
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-567cf35e3d7c4e39834ab4e5c36aa1ef
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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