Potassium Carbonate → 3-benzyl-5-({N-[4-(2-methoxy-ethoxy)-phenyl]-methylamino}-methylene)-2-thioxothiazolidin-4-one

HRID 600828Notes

Reaction equation

[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:14][N:15]([CH3:23])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[S:10][C:9]1=[S:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:31][O:32][CH2:33][CH2:34]Br>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:14][N:15]([CH3:23])[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:34][CH2:33][O:32][CH3:31])=[CH:20][CH:21]=2)[S:10][C:9]1=[S:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-benzyl-5-{[N-(4-hydroxyphenyl)-methylamino]-methylene}-2-thioxothiazolidin-4-one (71 mg, 0.20 mmol) in DMF (1.0 mL, anhyd) was added anhyd K2CO3 (29 mg, 0.21 mmol) and 2-bromoethyl methyl ether (20 μL, 0.21 mmol). The reaction mixture was heated at 50° C. After 20 h the reaction mixture was cooled, diluted with CHCl3 (50 mL), washed with H2O (3×25 mL) and brine, dried over anhyd Na2SO4, concentrated and then chromatographed (silica gel, 0:100 to 20:80 EtOAc-DCM) to give the title product (60 mg, 73%) as a yellow solid. 1H-NMR (CDCl3): δ 7.73 (1H, s), 7.44 (2H, d), 7.21-7.30 (3H, m), 7.11 (2H, d), 6.97 (2H, d), 5.23 (2H, s), 4.15 (2H, m), 3.79 (2H, m), 3.48 (3H, s), 3.47 (3H, s).

Workup

temperatureAfter 20 h the reaction mixture was cooled
washwashed with H2O (3×25 mL) and brine
dry with materialdried over anhyd Na2SO4
concentrationconcentrated
customchromatographed (silica gel, 0:100 to 20:80 EtOAc-DCM)

Sources & evidence

ORD record: ord-1348919a1856473ba4618a213d6eca1a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902237B2

Reaction notes

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