Lawesson's reagent → 8-fluoro-3-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione

HRID 1485437Notes

Reaction equation

HRID 1485437 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH:9]([CH3:12])[C:8](=O)[NH:7][C:6]=2[CH:14]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH:9]([CH3:12])[C:8](=[S:24])[NH:7][C:6]=2[CH:14]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 792909248-fluoro-3-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one

Product 1

HCID 867185058-fluoro-3-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-fluoro-3-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (6.2 g, 32 mmol) and Lawesson's reagent (25.9 g, 64 mmol) in tetrahydrofuran (300 mL) was heated at 80° C. for 1 hour. The mixture was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1-2:1) to afford 8-fluoro-3-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepine-2(3H)-thione as a pale green solid (10.0 g, crude).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1-2:1)

Sources & evidence

ORD record
ord-81274eac9c8d41c4b953a81ee06b2e1f
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

Loading…