Sulfuric Acid → 5-(4-Bromo-2-fluorophenyl)-1,3,4-thiadiazol-2-amine

HRID 1523742Notes

Reaction equation

OS(O)(=O)=O.[Br:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([NH:13][NH:14][C:15](=[S:17])[NH2:16])=O)=[C:9]([F:20])[CH:8]=1.N.O>C(O)(=O)CCCC>[Br:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]2[S:17][C:15]([NH2:16])=[N:14][N:13]=2)=[C:9]([F:20])[CH:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

H2SO4 (2 mL) was added to a solution of 2-(4-bromo-2-fluorobenzoyl)-hydrazinecarbothioamide (2.9 g, 10.0 mmol) in pentanoic acid (5 mL) and the resulting mixture was stirred at 110° Celsius for 2 hours. After cooling to rt, the reaction mixture was poured into ice-water (20 mL) and treated with NH3.H2O (15 mL). 5-(4-Bromo-2-fluorophenyl)-1,3,4-thiadiazol-2-amine was then isolated via vacuum filtration and air dried. MS (ESI): mass calcd. for C8H5BFN3OS, 272.94, m/z found, 274.1 [M+H]+.

Workup

temperatureAfter cooling to rt

Sources & evidence

ORD record: ord-33597772da764ea9bc015c0a2cb703d2
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079866B2

Reaction notes

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