P-Anisidine → HCID 11545509, compound

HRID 729283Notes

Reaction equation

HRID 729283 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].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1>CC#N>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=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 7732P-AnisidineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11545509HCID 11545509, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.300 g, 1.001 mmol), (4-methoxyphenyl)amine (0.136 g, 1.101 mmol) and TEA (0.140 ml, 1.001 mmol) in MeCN (3 ml) was heated in a microwave reactor at 120° C. for 20 mins, 130° C. for 30 mins, 140° C. for 30 mins and then using an oil bath at 120° C. for 24 h. The mixture was evaporated and the residue was purified by silica gel column chromatography using a 17% EtOAc in petroleum ether 40-60° C. as eluent, to give the title compound (0.152 g, 39%). 1H NMR (500 MHz, CDCl3): δ 7.24-7.14 (m, 1H), 7.12-7.08 (m, 1H), 7.07 (bs, 1H), 6.62 (d, 2H), 6.50 (d, 2H), 3.67 (s, 3H), 1.77 (s, 9H); 13C NMR (125 MHz CDCl3): δ 160.2, 157.2, 131.2, 129.6, 129.4, 128.9, 128.1, 125.1, 123.9, 113.8, 109.9, 61.9, 55.7, 27.9; Mass Spectrum: M+H+ 387.

Workup

  1. customat 120° C.
  2. customfor 24 h
  3. customThe mixture was evaporated
  4. customthe residue was purified by silica gel column chromatography
  5. customa 17% EtOAc in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-d6589161a5804ed2ba3ca8ee15bba251
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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