Lawesson's reagent → 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thione

HRID 1509300Notes

Reaction equation

HRID 1509300 reaction equation
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=O)[CH2:8][O:7][C:6]=2[N:12]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=[S:28])[CH2:8][O:7][C:6]=2[N:12]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 866836506-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

Product 1

HCID 866836666-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thioneYield 65.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (0.26 g, 0.852 mmol) and Lawesson's Reagent (0.34 g, 0.852 mmol) in toluene (10 ml) was heated at 120 degree for 16 h. The reaction mixture was concentrated to dryness and was added DCM (5 ml) and diisopropyl ether (20 ml). The precipitate was filtered to give product (0.18 g). 1H NMR (500 MHz, DMSO-d6): 12.9 (br, 1H), 7.35-7.55 (m, 5H), 7.32 (s, 1H), 5.16 (s, 2H).

Workup

  1. temperaturewas heated at 120 degree for 16 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additionwas added DCM (5 ml) and diisopropyl ether (20 ml)
  4. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-08875d6b041a4cb9b8c13ac7f0128d39
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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