4-Isopropoxyaniline → HCID 11668801, compound

HRID 729272Notes

Reaction equation

HRID 729272 reaction equation
[C: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])([CH3:4])([CH3:3])[CH3:2].[CH:20]([O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)([CH3:22])[CH3:21]>CC#N>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:28][C:27]2[CH:26]=[CH:25][C:24]([O:23][CH:20]([CH3:22])[CH3:21])=[CH:30][CH:29]=2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 821124-IsopropoxyanilineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11668801HCID 11668801, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.150 g, 0.50 mmol) and 4-isopropoxyaniline (0.151 g, 1.00 mmol) in MeCN (2 mL) was heated at 120° C. for 35 mins in a microwave reactor. The mixture was evaporated and the residue was purified by silica gel column chromatography using a 5:1 mixture of petroleum ether and EtOAc as eluant, to give the title compound (0.100 g, 48%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.20-7.14 (m, 1H), 7.12-7.08 (m, 4H), 7.04 (s, 1H), 6.62 (d, 1H), 6.48 (d, 2H), 4.34 (sep, 1H), 1.77 (s, 9H), 1.22 (d, 6H); 13C NMR (125 MHz, CDCl3): δ 160.1, 155.5, 131.4, 129.7, 129.3, 128.9, 128.1, 125.2, 124.1, 116.1, 109.9, 70.5, 61.9, 27.9, 22.0; Mass Spectrum: M−H+ 414.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by silica gel column chromatography
  3. additiona 5:1 mixture of petroleum ether and EtOAc as eluant

Sources & evidence

ORD record
ord-30aa67eff11c4384b1c4f2c5db0cb4fb
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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