Water → 3-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1,2,4-thiadiazole

HRID 908097Notes

Reaction equation

Cl[C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:3]=1.[NH:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[H-].[Na+].O>CS(C)=O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[N:3]=[C:2]([N:14]3[CH:18]=[CH:17][CH:16]=[CH:15]3)[S:6][N:5]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The 5-chloro-1,2,4-thiadiazole compound (102 mg, 0.445 mmol) was dissolved in DMSO (2 mL) and pyrrol (300 mg, 2.22 mmol) added at room temperature. The mixture was heated for 18 h to 55° C. ext. temperature, however no conversion was found (sample tested by 1H-NMR). Sodium hydride (55% wetted with mineral oil, 20 mg, 0.467 mmol) was added and the mixture heated to 80° C. ext. temperature for 5 h. As the conversion was not complete (sample tested by 1H-NMR) the mixture was heated to 100° C. ext. temperature for 6 h. The reaction mixture was poured into water (10 mL) and crude product isolated by filtration. The purification by column chromatography (SiO2, 0-10% ethyl acetate inheptanes) afforded 3-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1,2,4-thiadiazole (52 mg, 0.199 mmol, 45%), which was 98% pure (HPLC 254 nm). 1H-NMR spectra is in accordance with the chemical structure.

Workup

temperatureThe mixture was heated for 18 h to 55° C. ext
temperaturewas heated to 100° C. ext
waittemperature for 6 h
customisolated by filtration
customThe purification by column chromatography (SiO2, 0-10% ethyl acetate inheptanes)

Sources & evidence

ORD record: ord-6028836f3b0647c694547bed887d7c31
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017555B2

Reaction notes

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