1-Benzofuran-5-amine → 4-(1-Benzofuran-5-ylamino)-2-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729302Notes

Reaction equation

HRID 729302 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].[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([NH2:29])=[CH:28][C:23]=2[CH:22]=[CH:21]1>CC#N>[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([NH:29][C:8]3[C:9](=[O:10])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[S:6](=[O:19])(=[O:18])[C:7]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:28][C:23]=2[CH:22]=[CH:21]1

Participants

4

Reactant 2

HCID 14771521-Benzofuran-5-amineHCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 116109464-(1-Benzofuran-5-ylamino)-2-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.047 g, 0.141 mmol) and 1-benzofuran-5-amine (0.046 g, 0.345 mmol) in MeCN (1.5 ml) was heated in a microwave reactor at 130° C. for 60 mins and at 140° C. for 45 mins. The reaction mixture was evaporated and the residue was purified by column chromatography using EtOAc:heptane (1:3) as eluant. Crystallisation from hexane and EtOH gave the title compound (0.015 g, 27%). 1H NMR (400 MHz, CD3CN): 7.80 (bs, 1H), 7.65 (d, 1H), 7.17-7.09 (m, 4H), 7.07-7.02 (m, 3H), 6.85 (dd, 1H), 6.60-6.58 (m, 1H), 3.76 (t, 2H), 1.87-1.78 (m, 2H), 1.54-1.43 (m, 2H), 1.01 (t, 3H); Mass Spectrum: M+H+ 397.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by column chromatography
  3. customCrystallisation from hexane and EtOH

Sources & evidence

ORD record
ord-f34efe00f22a4119b89610a443fddceb
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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