Lawesson's reagent → HCID 10267348, compound

HRID 1258084Notes

Reaction equation

HRID 1258084 reaction equation
[CH3:1][C:2]1([CH3:22])[C:7]2[CH:8]=[C:9]([C:12]3[N:17]=[C:16]([CH2:18][C:19]#[N:20])[CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=O)[O:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>CC1C=CC(C)=CC=1>[CH3:1][C:2]1([CH3:22])[C:7]2[CH:8]=[C:9]([C:12]3[N:17]=[C:16]([CH2:18][C:19]#[N:20])[CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[S:32])[O:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22021893[6-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)pyridin-2-yl]acetonitrile

Product 1

HCID 10267348HCID 10267348, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

To [6-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)pyridin-2-yl]acetonitrile (80 mg, 0.27 mmol, 1 eq) in p-xylene (10 mL) was added Lawesson's reagent (55 mg, 0.14 mmol, 0.5 eq) and the reaction was heated to reflux for 2 hours. The reaction was cooled to room temperature and adsorbed onto silica gel. Purification by flash column chromatography (50% ethyl acetate/hexane) on silica gel gave the title compound (40 mg, 48%) as an off-white solid: mp 215-217° C.; 1H NMR (d6-DMSO, 300 MHz) δ 1.71 (s, 6H), 4.28 (s, 2H), 7.15 (d, 1H, J=8.3 Hz), 7.36 (d, 1H, J=7.3 Hz), 7.89-7.99 (m, 2H), 8.04-8.11 (m, 2H), 12.32 (s, 1H); MS (ESI) [M−H]−=308; Anal. Calcd. for C17H15N3OS: C, 66.00; H, 4.89; N, 13.58. Found: C, 64.43; H, 4.65; N, 12.95.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hours
  3. customPurification by flash column chromatography (50% ethyl acetate/hexane) on silica gel

Sources & evidence

ORD record
ord-968cc43ad9fb4c78a0ecc930a27ae1b0
Source dataset
uspto-grants-2013_06
Patent number
US08466146B2

Reaction notes

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