1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178431852, compound

HRID 1809568Notes

Reaction equation

HRID 1809568 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.CC1(C)O[C:31](=[O:33])[C:30](=[CH:34][NH:35][C:36]2[C:40]([CH3:41])=[CH:39][S:38][CH:37]=2)C(=O)O1>>[CH3:41][C:40]1[C:36]2=[N:35][CH:34]=[CH:30][C:31]([OH:33])=[C:37]2[S:38][CH:39]=1

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 669953662,2-Dimethyl-5-((4-methylthiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dione

Product 1

HCID 178431852HCID 178431852, compoundYield 101.9%

Conditions

Temperature
235 °C

Procedure

A solution of Dowtherm A (7 mL) was heated in oil bath at 235° C. under nitrogen. 2,2-Dimethyl-5-((4-methylthiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dione (5.0 g, 19 mmol) was added in portions over a 20 minutes period. After the last portion was added, the solution stirred at 235° C. for another 5 minutes. The solution was removed from the oil bath and allowed to cool to ambient temperature. Upon cooling, the product precipitated out of solution. Diethyl ether was added and the solid was filtered and dried to give the title compound (3.2 g) with residual amounts of Dowtherm A remaining.

Workup

  1. additionAfter the last portion was added
  2. customThe solution was removed from the oil bath
  3. temperatureto cool to ambient temperature
  4. temperatureUpon cooling
  5. customthe product precipitated out of solution
  6. additionDiethyl ether was added
  7. filtrationthe solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-24145346314942e09a272589d54a05ee
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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