Sodium Carbonate → 5-(4,4-diethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile

HRID 915899Notes

Reaction equation

HRID 915899 reaction equation
[CH2:1]([C:3]1([CH2:22][CH3:23])[C:8]2[CH:9]=[C:10]([C:13]3[N:17]([CH3:18])[C:16]([C:19]#[N:20])=[CH:15][CH:14]=3)[CH:11]=[CH:12][C:7]=2[NH:6][C:5](=O)[O:4]1)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1([CH2:22][CH3:23])[C:8]2[CH:9]=[C:10]([C:13]3[N:17]([CH3:18])[C:16]([C:19]#[N:20])=[CH:15][CH:14]=3)[CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[S:33])[O:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 87949Lawesson's reagentHCID 112553235-(4,4-diethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 104040655-(4,4-diethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrileYield 15.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(4,4-diethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile (0.5 g, 1.6 mmol) and Lawesson's Reagent (0.33 g, 0.81 mmol) were heated to 100° C. in toluene (20 mL). Upon completion by TLC, the reaction was poured into saturated sodium carbonate (100 mL) and extracted with ethyl acetate (50 mL), dried over magnesium sulfate, and concentrated. The purification with column gave 5-(4,4-diethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile (0.040 g, 8%) as a tan solid. 1H NMR (DMSO-d6): δ 12.15 (s, 1H), 7.44 (d, 1H, J=8.3, 1.8 Hz), 7.37 (d, 1H, J=1.8 Hz), 7.12 (d, 1H, J=8.3 Hz), 7.04 (d, 1H, J=4.03 Hz), 6.35 (d, 1H, J=4.2 Hz), 3.7 (s, 3H), 2.07 (m, 2H, J=7.4 Hz), 1.95 (m, 2H, J=7.4 Hz), 0.79 (t, 6H, J=7.4 Hz). MS (ESI) m/z 326 ([M+H]+); MS (ESI) m/z 324 ([M−H]−). HRMS: calcd for C18H19N3OS, 325.1249; found (ESI_FT), 326.13187.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe purification with column

Sources & evidence

ORD record
ord-452626498f6847f2bea55cfc48e10686
Source dataset
uspto-grants-2007_09
Patent number
US07268149B2

Reaction notes

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