Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1) → 3-Benzyl-1-methyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxoimidazolidin-4-one

HRID 1241988Notes

Reaction equation

HRID 1241988 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][N:10]([CH3:14])[C:9]1=[S:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH3:27][N+:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[S:30][C:29]=1SC>CC#N>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:29]2[N:28]([CH3:27])[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[S:30]2)[N:10]([CH3:14])[C:9]1=[S:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 41464Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)HCID 219376293-Benzyl-1-methyl-2-thioxoimidazolidin-4-one

Product 1

HCID 726398863-Benzyl-1-methyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxoimidazolidin-4-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of intermediate 3-benzyl-1-methyl-2-thioxoimidazolidin-4-one (0.33 g, 1.5 mmol) and 3-methyl-2-methylthiobenzothiazol-3-ium p-toluenesulfonate 0.66 g, 1.8 mmol) in anhydrous MeCN (10 mL) added dropwise TEA (0.28 mL, 2.0 mmol). After 2 h the resulting product mixture was concentrated and chromatographed (silica gel, DCM) to afford the title compound (0.47 g, 85%) as an orange-yellow solid. 1H-NMR (CDCl3): δ 7.54–7.61 (3H, m), 7.46 (1H, m), 7.21–7.33 (5H, m), 5.19 (2H, s), 3.86 (3H, s), 3.77 (3H, s).

Workup

  1. concentrationAfter 2 h the resulting product mixture was concentrated
  2. customchromatographed (silica gel, DCM)

Sources & evidence

ORD record
ord-6a3015ecb58b4fd38d76b3816b6ceae6
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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