2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 67318079, compound

HRID 1013645Notes

Reaction equation

HRID 1013645 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH2:11](OC(OCC)OCC)C.[F:21][C:22]1[CH:23]=[C:24]([CH:26]=[C:27]([F:29])[CH:28]=1)[NH2:25]>CCCCCC>[F:21][C:22]1[CH:23]=[C:24]([NH:25][CH:11]=[C:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])[CH:26]=[C:27]([F:29])[CH:28]=1

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 965953,5-Difluoroaniline

Product 1

HCID 67318079HCID 67318079, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

In a oven dried 2-neck RBF equipped with reflux condenser and inert atmosphere, meldrum's acid (30 g, 0.208 mole) was dissolved in triethylorthoformate (185 g, 1.25 mole) and the reaction mixture was refluxed at 100° C. under nitrogen for 1 h. On complete consumption of starting material (tic), 3,5-difluoroaniline (26.8 g, 0.208 mol) was added and the heating continued for 4 h. After completion of the reaction (tic), reaction mixture was brought to RT and diluted with hexane (300 ml) when yellow solid precipitated. The solid was filtered, washed thoroughly with hexane and dried to furnish the product.

Workup

  1. customIn a oven dried 2-neck RBF
  2. customequipped
  3. temperaturewith reflux condenser
  4. additionwas added
  5. customAfter completion of the reaction (tic), reaction mixture
  6. customwas brought to RT
  7. customprecipitated
  8. filtrationThe solid was filtered
  9. washwashed thoroughly with hexane
  10. customdried
  11. customto furnish the product

Sources & evidence

ORD record
ord-e05a6e734e1243fd91dc67f20a8383cb
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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