Ethanol → N-methyl-N-[4-[[(Z)-(7-oxo-6H-pyrrolo[2,3-g][1,3]benzothiazol-8-ylidene)methyl]amino]phenyl]acetamide

HRID 1246985Notes

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].[CH2:18]([OH:20])[CH3:19]>C(OCC)C>[CH3:4][N:5]([C:6]1[CH:14]=[CH:13][C:9]([NH:10]/[CH:11]=[C:3]2\[C:4](=[O:16])[NH:5][C:6]3[C:14]\2=[C:13]2[S:12][CH:11]=[N:10][C:9]2=[CH:8][CH:7]=3)=[CH:8][CH:7]=1)[C:18](=[O:20])[CH3:19]

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, 6.040 g, 0.163 mmol), 4-amino-N-methylacetanilide (0.040 g, 0.244 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 0.038 g (64%) of the title compound. 1H NMR (DMSO-d6): δ 11.03 (d, 1H, J=12.3 Hz), 10.84 (s, 1H), 9.23 (s, 1H), 8.02 (d, 1H, J=12.3 Hz), 7.78 (d, 1H, J=8.4 Hz), 7.48 (d, 2H, J=8.2 Hz), 7.35 (d, 2H, J=8.2 Hz), 7.09 (d, 1H, J=8.4 Hz), 3.11 (s, 3H), 1.76 (s, 3H); ES-MS m/z 363 (M−H).

Workup

filtrationthe product collected by filtration

Sources & evidence

ORD record: ord-c1c4fcd54ff8479f9d18fef88740d2ce
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129253B2

Reaction notes

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