3-Methoxyphenol → HCID 11683726, compound

HRID 2422028Notes

Reaction equation

HRID 2422028 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](O)[CH:6]=[CH:7][CH:8]=1.CC1C=CC(S([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]2[C:26](=[O:42])[N:27]([C:38]([CH3:41])([CH3:40])[CH3:39])[S:28](=[O:37])(=[O:36])[C:29]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=O)=O)=CC=1>>[C:38]([N:27]1[C:26](=[O:42])[C:25]([NH:24][CH2:23][CH2:22][CH2:21][O:20][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=2)=[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[S:28]1(=[O:37])=[O:36])([CH3:41])([CH3:40])[CH3:39]

Participants

3

Reactant 2

HCID 90073-MethoxyphenolHCID 866258673-[(2-Tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate

Product 1

HCID 11683726HCID 11683726, compoundYield 65%

Procedure

The title compound was prepared as described for Example 12 from 3-methoxyphenol and 3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate with a reaction time of 15 mins. The reaction mixture was evaporated and the crude product was purified by silica gel column chromatography (Horizons Biotage) using 15% EtOAc in petroleum ether 40-60° C. as eluent to give the title compound (0.070 g, 65%). 1H NMR (500 MHz CDCl3): δ 7.54-7.45 (m, 2H), 7.45 (m, 3H), 7.18 (t, 1H), 6.53 (dd, 1H), 6.48-6.42 (m, 2H), 5.79 (t, 1H), 3.89 (t, 2H), 3.82 (s, 3H), 3.12-3.06 (m, 2H), 1.86-1.82 (m, 2H), 1.75 (s, 9H); 13C NMR (125 MHz CDCl3): δ 161.1, 159.8, 159.7, 135.3, 131.8, 130.2, 129.7, 128.8, 125.3, 107.2, 107.1, 106.6, 101.2, 66.2, 61.7, 55.5, 42.6, 28.9, 27.8; Mass Spectrum M+H+ 445.

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was evaporated
  3. customthe crude product was purified by silica gel column chromatography (Horizons Biotage)
  4. custom15% EtOAc in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-7c23d12a42034456a188026eac15e029
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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