Ethanol → (8Z)-8-[[4-(3-methyl-5-oxo-1H-pyrazol-2-yl)anilino]methylidene]-6H-pyrrolo[2,3-g][1,3]benzothiazol-7-one

HRID 840912Notes

Reaction equation

CN(C)[CH:3]1[C:14]2[C:6](=[CH:7][CH:8]=[C:9]3[C:13]=2[S:12](=C)[CH:11]=[N:10]3)[NH:5][C:4]1=[O:16].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:29]([CH3:30])=[CH:28][C:27](=[O:31])[NH:26]2)=[CH:21][CH:20]=1.[CH2:32](O)C>C(OCC)C>[CH3:30][C:29]1[N:25]([C:22]2[CH:21]=[CH:20][C:19]([NH:18]/[CH:32]=[C:3]3\[C:4](=[O:16])[NH:5][C:6]4[C:14]\3=[C:13]3[S:12][CH:11]=[N:10][C:9]3=[CH:8][CH:7]=4)=[CH:24][CH:23]=2)[NH:26][C:27](=[O:31])[CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 8-dimethylamino-methylene-6,8-dihydro-1-thia-3,6-diaza-as-indacen-7-one (Procedure E, 0.040 g, 0.163 mmol), 2-(4-aminophenyl)-3-methyl-pyrazoline-5-one (0.047 g, 0.248 mmol) in absolute ethanol (5 ml) was heated with stirring at 90° C. for 16 h. The reaction was diluted with ethanol and diethyl ether and the product collected by filtration to yield 0.052 (83%) of the title compound. 1H NMR (DMSO-d6): δ11.08 (d,1H, J=12.3 Hz), 10.84 (s,1H), 9.85 (s,1H), 9.23 (s,1H), 8.05 (d,1H, J=12.1 Hz), 7.78 (d,1H, J=8.2 Hz), 7.51-7.45 (m,4H), 7.10 (d,1H, J=8.4 Hz), 5.55 (s,1H), 2.25 (s,3H); ES−MS m/z 388 (M−H).

Workup

temperaturewas heated
filtrationthe product collected by filtration

Sources & evidence

ORD record: ord-900c1cc488b7407c972355463e8f3455
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369086B1

Reaction notes

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