Ethyl Acetate → HCID 11655580, compound

HRID 729299Notes

Reaction equation

HRID 729299 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]([O:27][C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O>CN(C=O)C>[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([NH:34][C:8]2[C:9](=[O:10])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[S:6](=[O:19])(=[O:18])[C:7]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:32][CH:33]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 228604-BenzyloxyanilineHCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11655580HCID 11655580, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.600 g, 2.001 mmol), [4-(benzyloxy)phenyl]amine (1.415 g, 6.004 mmol) and TEA (0.840 ml, 6.004 mmol) in DMF (5 ml) was heated in a microwave reactor at 140° C. for 25 mins. EtOAc was added to the mixture, and it was washed with brine, evaporated and the residue was purified by flash chromatography using a 5:1 EtOAc/petroleum ether 40-60° C. mixture as eluent to give the title compound (0.721 g, 78%). 1H NMR (500 MHz CDCl3); δ 7.42-7.33 (m, 4H), 7.22-7.17 (m, 1H), 7.15-7.09 (m, 5H), 6.65 (d, 2H), 6.61 (d, 2H), 4.96 (s, 2H), 3.79 (t, 2H), 1.92-1.84 (m, 2H), 1.54-1.44 (m, 2H), 1.01 (t, 3H); Mass Spectrum M+H+ 463.

Workup

  1. washwas washed with brine
  2. customevaporated
  3. customthe residue was purified by flash chromatography
  4. customa 5:1 EtOAc/petroleum ether 40-60° C. mixture

Sources & evidence

ORD record
ord-b63fa7d08004436ca4054e639b02c5dc
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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