Methanol → 2-Butyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

HRID 416591Notes

Reaction equation

HRID 416591 reaction equation
[CH2:1]([N:5]1[C:14](=O)[C:13]([C:16]#[N:17])=[C:12]2[C:7]([CH:8](O)[CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1.CO>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:14](=[S:28])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 87949Lawesson's reagentHCID 222665102-Butyl-8-hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

Product 1

HCID 222665172-Butyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrileYield 73.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Butyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-013) (80 mg, 0.35 mmol) was dissolved in toluene (8 mL), and to the reaction mixture was added Lawesson's reagent (169 mg, 0.42 mmol), the reaction mixture was heated under reflux for 12 h. The reaction mixture was cooled to room temperature, and methanol was added to the reaction mixture, and the reaction mixture was stirred at room temperature for 1 h, and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 2-butyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-014) (63 mg, 73%) as a pale brown powder.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 12 h
  3. customevaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-96af06376f93472ebc0ba07f408fa3c7
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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