Diphenylmethylidenehydrazine → (E)-N-[(E)-(3-bromothiophen-2-yl)methylideneamino]-1,1-diphenylmethanimine

HRID 2173030Notes

Reaction equation

[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.[C:9]1([C:15](=[N:22][NH2:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[CH:7]=[N:23]/[N:22]=[C:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Bromothiophene-2-carbaldehyde (8.0 g, 41.9 mmol) and (diphenylmethylene)hydrazine (9.45 g, 48.2 mmol) were dissolved in ethanol (60 mL) and the solution was heated at 80° C. overnight. Volatiles from the reaction mixture were removed via rotary evaporation and the crude product was purified by normal phase silica gel chromatography (ISCO-Combiflash) eluting with a gradient of 0-30% hexane and EtOAc. The pure fractions were combined and evaporated to give the title compound as a mixture of cis/trans isomers (15.0 g, 97%). ESI-MS m/z [M+H]+ calc'd for C18H13BrN2S, 370. found, 370.

Workup

customVolatiles from the reaction mixture were removed via rotary evaporation
customthe crude product was purified by normal phase silica gel chromatography (ISCO-Combiflash)
washeluting with a gradient of 0-30% hexane and EtOAc
customevaporated

Sources & evidence

ORD record: ord-3f030bd3ddb543b894cc6cdfb2ce137d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056873B2

Reaction notes

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