4-Aminophenol hydrochloride → 2-Butyl-4-[(hydroxyphenyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729276Notes

Reaction equation

HRID 729276 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4].Cl.O[C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.CN(C=[O:33])C>>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:26][C:25]2[CH:27]=[CH:28][CH:22]=[CH:23][C:24]=2[OH:33])=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 58284-Aminophenol hydrochlorideHCID 6228DimethylformamideHCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 686619952-Butyl-4-[(hydroxyphenyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 57%

Conditions

Temperature
140 °C

Procedure

A mixture of 2-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.110 g, 0.33 mmol), 4-hydroxyaniline hydrochloride (0.144 g, 0.99 mmol) and TEA (0.14 ml, 0.991 mmol) in DMF (0.5 ml) was heated at 140° C. for 25 mins in a microwave reactor. The mixture was purified by preparative HPLC (column Ace C8, 0.1M NH4OAc/MeCN, gradient) to give the title compound (0.074 g, 57%); 1H NMR 400 MHz (CDCl3) 7.26-7.20 (m, 2H), 7.18-7.14 (m, 3H), 7.08 (s, 1H), 6.62 (d, 2H), 6.48 (d, 2H), 3.78 (t, 2H), 1.91-1.84 (m, 2H), 1.53-1.45 (m, 2H), 1.02 (t, 3H); Mass Spectrum: M+H 373.

Workup

  1. customThe mixture was purified by preparative HPLC (column Ace C8, 0.1M NH4OAc/MeCN, gradient)

Sources & evidence

ORD record
ord-b593360e6eff4af5bdc08b7ea5d54281
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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