Diphenylmethylidenehydrazine → N-benzhydrylidene-N'-[1-[3-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-thiophen-2-yl]-methylidene]-hydrazine

HRID 2078733Notes

Reaction equation

HRID 2078733 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:15])([CH3:14])[O:8][SiH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[S:4][C:3]=1[CH:16]=O.[C:18](=[N:31][NH2:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[C:18](=[N:31][N:32]=[CH:16][C:3]1[S:4][C:5]([C:7]([CH3:15])([CH3:14])[O:8][SiH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][C:2]=1[Br:1])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 79304DiphenylmethylidenehydrazineHCID 1317274143-Bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-thiophene-2-carbaldehyde2×

Product 1

HCID 131727413N-benzhydrylidene-N'-[1-[3-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-thiophen-2-yl]-methylidene]-hydrazineYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-thiophene-2-carbaldehyde [30.1 g, 89.7 mmol, Intermediate (68)] in ethanol (350 mL) was added benzophenone hydrazone (20 g, 104.7 mmol). The resulting yellow solution was stirred at reflux for 6 hours. The solvent was then removed and the residue was chromatographed through silica gel (n-heptane/dichloromethane, 20/80 as eluant) to produce N-benzhydrylidene-N′-[1-[3-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-thiophen-2-yl]-methylidene]-hydrazine [41.3 g, Intermediate (69)]. LC/MS: 515.1 (M+H), (2 isomers detected) RT=4.17 minutes and 4.34 minutes.

Workup

  1. temperatureat reflux for 6 hours
  2. customThe solvent was then removed
  3. customthe residue was chromatographed through silica gel (n-heptane/dichloromethane, 20/80 as eluant)

Sources & evidence

ORD record
ord-04e0464144c0402083c4bb30a609d644
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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