Lawesson's reagent → ethyl 1-[4-(1H-pyrazol-1-yl)benzyl]-4-thioxo-1,4-dihydrocinnoline-3-carboxylate

HRID 449940Notes

Reaction equation

O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[CH:22][CH:21]=[N:20]3)=[CH:15][CH:14]=2)[N:4]=[C:3]1[C:24]([O:26][CH2:27][CH3:28])=[O:25].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:38]2)=CC=1>C1(C)C=CC=CC=1>[N:19]1([C:16]2[CH:15]=[CH:14][C:13]([CH2:12][N:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2](=[S:38])[C:3]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:4]3)=[CH:18][CH:17]=2)[CH:23]=[CH:22][CH:21]=[N:20]1

Participants

Conditions

Temperature: 105 °C

Procedure

Ethyl 4-oxo-1-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-1,4-dihydrocinnoline-3-carboxylate (253 mg, 0.676 mmol) was suspended in toluene (3 mL) and treated with 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (Lawesson's Reagent, 164 mg, 0.405 mmol, 0.6 equiv). The mixture was heated at 105° C. for 1 hour, cooled to ambient temperature, and concentrated in vacuo. The residue was purified by silica gel chromatography (90:10 to 60:40; hexanes:ethyl acetate), providing the titled compound.

Workup

temperaturecooled to ambient temperature
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (90:10 to 60:40; hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-cf55f884843b4a449108014c702fa35a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486946B2

Reaction notes

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