Tesmilifene Hydrochloride → 5-Bromo-2-nitrothiophene-3-carboxamide

HRID 1799539Notes

Reaction equation

[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([CH:10]=[N:11]O)[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=[O:21])=CC=1.CCN(CCOC1C=CC(CC2C=CC=CC=2)=CC=1)CC.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:11])=[O:21])[CH:3]=1

Participants

Conditions

Temperature: 111 °C

Procedure

5-Bromo-2-nitrothiophene-3-carbaldehyde oxime (45 g, 179 mmol), p-toluenesulfonic acid monohydrate (2.73 g, 14.34 mmol), dppe (1.428 g, 3.58 mmol) and Ru(PPh3)3(CO)H2 (3.29 g, 3.58 mmol) were taken up in toluene (750 mL). The flask was evacuated and back-filled with N2 (3×) before stirring at 111° C. under N2 for 24 hours. After cooling to room temperature, the reaction mixture was purified directly by flash silica gel column chromatography (0-100% EtOAc/toluene) to give the title compound as brown needles after recrystallising from EtOH-hexanes.

Workup

customThe flask was evacuated
additionback-filled with N2 (3×)
temperatureAfter cooling to room temperature
customthe reaction mixture was purified directly by flash silica gel column chromatography (0-100% EtOAc/toluene)

Sources & evidence

ORD record: ord-72d13c87413e45a1a563a2d1129933c9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344144B2

Reaction notes

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