4-Toluenesulfonyl chloride → 2-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl 4-methylbenzenesulfonate

HRID 2239537Notes

Reaction equation

HRID 2239537 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](OCCCNC2C(=O)N(C(C)(C)C)S(=O)(=O)C=2C2C=CC=CC=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:34]([N:38]1[C:42](=[O:43])[C:41]([NH:44][CH2:45][CH2:46][OH:47])=[C:40]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[S:39]1(=[O:55])=[O:54])([CH3:37])([CH3:36])[CH3:35].CC1C=CC(S(Cl)(=O)=O)=CC=1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:47][CH2:46][CH2:45][NH:44][C:41]2[C:42](=[O:43])[N:38]([C:34]([CH3:37])([CH3:35])[CH3:36])[S:39](=[O:54])(=[O:55])[C:40]=2[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 672439862-tert-butyl-4-[(2-hydroxyethyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxideHCID 866258673-[(2-Tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate

Product 1

HCID 866258662-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl 4-methylbenzenesulfonateYield 76%

Procedure

The title compound was prepared as described for 3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate from 2-tert-butyl-4-[(2-hydroxyethyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxide (Example 76) and 4-methylbenzenesulfonyl chloride with a reaction time of 17 h. The reaction mixture was purified by silica gel column chromatography (Horizons Biotage) using 50-100% DCM in petroleum ether 40-60° C. as eluent to give the title compound (1.93 g, 76%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.76 (d, 1H), 7.46-7.35 (m, 7H), 5.44 (t, 1H), 3.85 (t, 2H), 3.18-3.12 (m, 2H), 2.49 (s, 3H), 1.74 (s, 9H); Mass Spectrum M+H+ 479.

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was purified by silica gel column chromatography (Horizons Biotage)
  3. custom50-100% DCM in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-8c4b86db7b764bd09ff0ccd97178caf4
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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