Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1) → 3-[3-butyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]benzonitrile

HRID 2121925Notes

Reaction equation

[CH2:1]([N:5]1[C:9](=[O:10])[CH2:8][S:7][C:6]1=[N:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16])[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH3:31][N+:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[S:34][C:33]=1SC>CC#N>[CH2:1]([N:5]1[C:9](=[O:10])[C:8](=[C:33]2[N:32]([CH3:31])[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[S:34]2)[S:7][C:6]1=[N:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 8 mL vial was added 3-(3-butyl-4-oxothiazolidin-2-ylideneamino)benzonitrile (55 mg, 0.20 mmol), 3-methyl-2-(methylthio)benzothiazol-3-ium p-toluenesulfonate (73 mg, 0.20 mmol), anhydrous MeCN (2 mL) and TEA (70 μL, 0.50 mmol). The reaction mixture was first Warmed to 50° C. and the resulting solution was allowed to stir at room temperature for 16 h. The product mixture was concentrated under reduced pressure, chromatographed (silica gel, 1:99 MeOH/DCM) and then recrystallized from MeCN to give the title product (11.8 mg) as a yellow solid. 1H-NMR (CDCl3): δ 7.52 (1H, dd), 7.38-7.48 (2H, m), 7.32-7.37 (2H, m), 7.25 (1H, m), 7.18 (1H, m), 7.06 (1H, d), 3.96 (2H, t), 3.75 (3H, s), 1.77 (2H, m), 1.44 (2H, m), 0.98 (3H, t); MS(ESI): 421 (MH+).

Workup

concentrationThe product mixture was concentrated under reduced pressure
customchromatographed (silica gel, 1:99 MeOH/DCM)
customrecrystallized from MeCN

Sources & evidence

ORD record: ord-375e843496814e82a42151e681a49262
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696473B2

Reaction notes

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