Lawesson's reagent → N-[2,6-Dimethyl-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-3,3-dimethyl-thiobutanamide

HRID 2067834Notes

Reaction equation

HRID 2067834 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([CH3:22])[C:3]=1[NH:23][C:24](=O)[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>ClC(Cl)C>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([CH3:22])[C:3]=1[NH:23][C:24](=[S:40])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 24937078N-[2,6-Dimethyl-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-3,3-dimethyl butanamide

Product 1

HCID 58097357N-[2,6-Dimethyl-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-3,3-dimethyl-thiobutanamide

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of N-[2,6-Dimethyl-4-(6-trifluoromethyl-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-3,3-dimethyl-butyramide (200 mg, 0.48 mmol) in dichloroethane (10 mL) was added Lawesson's reagent (193 mg, 0.48 mmol) and the reaction mixture was stirred at reflux for 2 h. The mixture was then cooled to room temperature and concentrate. Purification by preparative thin layer chromatography (dichloromethane 100%) afforded the desired compound as a solid.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrate
  3. customPurification by preparative thin layer chromatography (dichloromethane 100%)

Sources & evidence

ORD record
ord-999ae8736b464c77a740e69d6f468c5e
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

Loading…