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

HRID 246053Notes

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

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 3-bromothiophene-2-carbaldehyde (5.57 g, 29.2 mmol) in EtOH (90 mL) was added (diphenylmethylene)hydrazine (6.3 g, 32.1 mmol). The reaction mixture was heated at 65° C. for 4 h then concentrated. The residue was purified by silica gel chromatography with 10% to 20% EtOAc/heptane to afford 11 g of N-benzhydrylidene-N′-[1-(3-bromo-thiophen-2-yl)-meth-(E)-ylidene]-hydrazine as a viscous yellow oil.

Workup

concentrationthen concentrated
customThe residue was purified by silica gel chromatography with 10% to 20% EtOAc/heptane

Sources & evidence

ORD record: ord-b14e32d6686a48e0b9c7587d5d0057d1
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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