N-Methylaniline → 3-benzyl-5-[(N-methyl-phenylamino)-methylene]-2-thioxo-thiazolidin-4-one

HRID 600823Notes

Reaction equation

HRID 600823 reaction equation
[CH3:1][C@H](NC([C@H]1N(C([C@@H](NC([C@@H](N)CC2C=CC(O)=CC=2)=O)CC(O)=O)=O)CCC1)=O)C(N1[C@H](C(N2[C@H](C(N3[C@H](C(N4[C@H](C(N5[C@H](C(N6[C@H](C(O)=O)CCC6)=O)CCC5)=O)CCC4)=O)CCC3)=O)CCC2)=O)CCC1)=O.C1(C)C=CC=CC=1.[CH3:83][NH:84][C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1.[CH2:91]([N:98]1[C:102](=[O:103])[CH2:101][S:100][C:99]1=[S:104])[C:92]1[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=1>>[CH2:91]([N:98]1[C:102](=[O:103])[C:101](=[CH:83][N:84]([C:85]2[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=2)[CH3:1])[S:100][C:99]1=[S:104])[C:92]1[CH:93]=[CH:94][CH:95]=[CH:96][CH:97]=1

Participants

4

Reactant 3

HCID 7515N-MethylanilineHCID 976733-(Phenylmethyl)-2-thioxo-4-thiazolidinoneHCID 131728738TMOF toluene

Product 1

HCID 723711903-benzyl-5-[(N-methyl-phenylamino)-methylene]-2-thioxo-thiazolidin-4-oneYield 39%

Procedure

To a mixture of TMOF-toluene (1:1, 6 mL, anhyd) was added N-methylaniline (0.33 mL, 3.0 mmol) and 3-benzylrhodanine (0.67 g, 3.0 mmol). After heating at reflux for 2 h, the reaction mixture was cooled, concentrated and chromatographed (silica gel, 0:100 to 40:60 EtOAc-Hex) to yield the title product (0.40 g, 39%) as a yellow solid. 1H-NMR (CDCl3): δ 7.79 (1H, s), 7.34-7.47 (5H, m), 7.17-7.31 (5H, m), 5.25 (2H, s), 3.54 (3H, s).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. temperaturethe reaction mixture was cooled
  4. concentrationconcentrated
  5. customchromatographed (silica gel, 0:100 to 40:60 EtOAc-Hex)

Sources & evidence

ORD record
ord-90191e4d4f014fd1b62758049163b41c
Source dataset
uspto-grants-2011_03
Patent number
US07902237B2

Reaction notes

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