4-(Methylthio)phenylhydrazine → 6-fluoro-2-[1-(4-methylthiophenyl)-3-trifluoromethyl-1H-pyrazol-5-yl]benzothiazole

HRID 369079Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9](=O)[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])[S:8][C:4]=2[CH:3]=1.[CH3:20][S:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1>C(O)(=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[N:28]([C:25]4[CH:26]=[CH:27][C:22]([S:21][CH3:20])=[CH:23][CH:24]=4)[N:29]=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=3)[S:8][C:4]=2[CH:3]=1.[F:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:28]([C:25]4[CH:26]=[CH:27][C:22]([S:21][CH3:20])=[CH:23][CH:24]=4)[N:29]=3)[S:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 1-(6-fluorobenzothiazol-2-yl)-4,4,4-trifluorobutane-1,3-dione (820 mg, 2.82 mmol) and 4-methylthio-phenylhydrazine (529.5 mg, 3.43 mmol) in acetic acid (23 ml) was stirred at 100° C. for 13 hours, allowed to cool and then concentrated. The resulting residue was subjected to purification using column chromatography on silica gel to afford 6-fluoro-2-[1-(4-methylthiophenyl)-3-trifluoromethyl-1H-pyrazol-5-yl]benzothiazole (500 mg, 43%) and 6-fluoro-2-[1-(4-methylthiophenyl)-5-trifluoromethyl-1H-pyrazol-3-yl]-benzothiazole (58 mg, 5%).

Workup

temperatureto cool
concentrationconcentrated
customThe resulting residue was subjected to purification

Sources & evidence

ORD record: ord-286cf20a1d684d37b9452dabfccfde68
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136831

Reaction notes

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