Diphenylmethylidenehydrazine → HCID 89330309, compound

HRID 2173033Notes

Reaction equation

HRID 2173033 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=O)[CH3:8].[C:10]1([C:16](=[N:23][NH2:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[C:7](=[N:24]/[N:23]=[C:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)/[CH3:8]

Participants

4

Reactant 2

HCID 79304DiphenylmethylidenehydrazineHCID 27644962-Acetyl-3-bromothiophene

Product 1

HCID 89330309HCID 89330309, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(3-Bromothiophen-2-yl)ethanone (8.0 g, 39.0 mmol) and (diphenylmethylene)hydrazine (8.42 g, 42.9 mmol) were dissolved in ethanol (75 mL). The reaction mixture was heated in an oil bath at 80° C. for 16 hours. Following reaction, the volatiles were evaporated, and the condensed mixture was purified via silica gel column chromatography, eluting with a gradient of 0-100% hexane and EtOAc. The pure fractions were combined and evaporated to give the title compound as a yellow solid (12.5 g, 84%). ESI-MS m/z [M+H]+ calc'd for C19H15BrN2S, 384. found, 384.

Workup

  1. customreaction
  2. customthe volatiles were evaporated
  3. customthe condensed mixture was purified via silica gel column chromatography
  4. washeluting with a gradient of 0-100% hexane and EtOAc
  5. customevaporated

Sources & evidence

ORD record
ord-2913eb132f2046a9906987d3276dd34d
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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