Pyridine → 3-(3-Butyl-4-oxothiazolidin-2-ylideneamino)benzonitrile

HRID 1241948Notes

Reaction equation

HRID 1241948 reaction equation
[CH2:1]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=1)=[S:7])[CH2:2][CH2:3][CH3:4].Cl[CH2:18][C:19](OCC)=[O:20].N1C=CC=CC=1>CCO>[CH2:1]([N:5]1[C:19](=[O:20])[CH2:18][S:7][C:6]1=[N:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:15]#[N:16])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7751Ethyl chloroacetateHCID 23461541-Butyl-3-(3-cyanophenyl)thiourea

Product 1

HCID 219374063-(3-Butyl-4-oxothiazolidin-2-ylideneamino)benzonitrileYield 67.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100 mL flask was added anhydrous EtOH (25 mL), 1-butyl-3-(3-cyanophenyl)thiourea (0.99 g, 4.2 mmol), ethyl chloroacetate (0.51 mL, 5.0 mmol), and anhydrous pyridine (0.5 mL, 5 mmol). After heating under reflux 16 h, the product mixture was concentrated under reduced pressure and chromatographed (silica gel, 2:98 MeOH/DCM) to afford the title product (0.78 g, 67%) as a colorless oil. 1H-NMR (CDCl3): δ 7.40–7.47 (2H, m), 7.25 (1H, m), 7.19 (1H, m), 3.84 (2H, t), 3.84 (2H, s), 1.69 (2H, m), 1.39 (2H, m), 0.97 (3H, t); MS(ESI): 274 (MH+).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux 16 h
  3. concentrationthe product mixture was concentrated under reduced pressure
  4. customchromatographed (silica gel, 2:98 MeOH/DCM)

Sources & evidence

ORD record
ord-bd61a0ff4d004afb8d771b5d0698a09d
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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