Potassium Carbonate → 2-Tert-butyl-5-[3-(3-hydroxy-propoxy)-phenyl]-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

HRID 724616Notes

Reaction equation

HRID 724616 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][CH2:22][CH2:23][OH:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:21][CH2:22][CH2:23][OH:24])[CH:12]=2)[S:6]1(=[O:18])=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 587467962-Tert-butyl-5-(3-hydroxy-phenyl)-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

Product 1

HCID 587468372-Tert-butyl-5-[3-(3-hydroxy-propoxy)-phenyl]-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-oneYield 88.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4.08-B (0.2 g, 0.7 mmol), 3-bromo-1-propanol (0.1 mL, 1.1 mmol), and potassium carbonate (147 mg, 1.1 mmol) in N,N-dimethylformamide (3 mL) was heated at 80° C. for 1 h. The reaction mixture was diluted with ethyl acetate (75 mL) and washed with 0.5 N HCl (50 mL) and brine (50 mL), dried with Na2SO4, filtered, and concentrated to give a crude residue which was purified using flash column chromatography (100% hexane to 50% ethyl acetate/hexane) to yield 4.08-C as a white solid (0.21 g, 88%). 1H NMR (500 MHz, CDCl3): δ 7.42 (dd, J=7.8, 7.8 Hz, 1H), 7.36–7.34 (m, 1H), 7.30 (dd, J=2.0, 2.0 Hz, 1H), 7.11–7.09 (m, 1H), 6.63 (s, 1H), 4.18–4.12 (m, 2H), 3.90–3.86 (m, 2H), 2.10–2.05 (m, 2H), 1.73 (s, 9H); LCMS found for C16H22NO5S (M+H)+: m/z=340.

Workup

  1. washwashed with 0.5 N HCl (50 mL) and brine (50 mL)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude residue which
  6. customwas purified

Sources & evidence

ORD record
ord-08acf56d297742998d9c7af9b38ad1cc
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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