1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 21873662, compound

HRID 639015Notes

Reaction equation

HRID 639015 reaction equation
[Br:1][C:2]1[C:3]([NH:12][CH:13]=[C:14]2[C:19](=[O:20])OC(C)(C)OC2=O)=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.C(OCC)(=O)C.CCCCCC>CO>[Br:1][C:2]1[CH:11]=[C:6]2[O:7][CH2:8][CH2:9][O:10][C:5]2=[C:4]2[C:3]=1[NH:12][CH:13]=[CH:14][C:19]2=[O:20]

Participants

5

Reactant 3

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 21226206Ethyl acetate hexaneHCID 21873810HCID 21873810, compound

Product 1

HCID 21873662HCID 21873662, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-[(7-Bromo-2,3-dihydro-benzo[1,4]dioxin-6-ylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (22.9 g, 59.6 mmol) was added portionwise to refluxing Dowtherm A® (45 mL) over 3 minutes. After a further 3 minutes at reflux the mixture was cooled to room temperature. Ethyl acetate/hexane (10 mL/20 mL) was added and a black solid isolated by filtration. This residue was dissolved in hot methanol (400 mL) and filtered through Keiselguhr. Water (800 mL) was added and the mixture stored at 5° C. overnight. Filtration and drying afforded a pale yellow solid (10.3 g, 61%).

Workup

  1. temperatureAfter a further 3 minutes at reflux the mixture
  2. customa black solid isolated by filtration
  3. filtrationfiltered through Keiselguhr
  4. additionWater (800 mL) was added
  5. filtrationFiltration
  6. customdrying

Sources & evidence

ORD record
ord-83a9b817fb3e49498eda024cc2b243df
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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