Hexylamine → 2-Butyl-4-(hexylamino)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 2239616Notes

Reaction equation

HRID 2239616 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].[CH2:20]([NH2:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:26][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[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 2

HCID 8102HexylamineHCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 115161072-Butyl-4-(hexylamino)-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.110 g, 0.33 mmol) and hexylamine (0.100 g, 0.984 mmol) in DMF (0.5 mL) was heated in a microwave reactor at 140° C. for 25 mins. The residue was purified by preparative HPLC (Ace C8 column, 0.1M NH4OAc/MeCN, gradient) to give the title compound (0.060 g, 47%); 1H-NMR (400 MHz, CD3CN): δ 7.49-7.53 (m, 5H), 5.85 (bs, 1H), 3.66 8 (t, 2H), 2.85 (dd, 2H), 1.71-1.80 (m, 2H), 1.37-1.48 (m, 2H), 1.13-1.34 (m, 4H), 0.94-1.09 (m, 7H), 0.82 (t, 3H); Mass Spectrum: M+H 365.

Workup

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

Sources & evidence

ORD record
ord-e450a795edb7480eb5aa4946c036f78b
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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