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

HRID 1967148Notes

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-5330a41d2d2f4e5bb5b80c561703fd93
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420695B2

Reaction notes

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