Phosphorus oxide (P4O10) → HCID 2794459, compound

HRID 1357768Notes

Reaction equation

HRID 1357768 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].[CH:12]([CH:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15]([O-])=O)=[O:13].C[Si](OP(=O)=O)(C)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[Si](C)(C)O[Si](C)(C)C.C(=O)([O-])O.[Na+]>ClCCCl>[CH3:11][O:10][C:8]1[CH:9]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:7]=1[CH:15]=[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12](=[O:13])[NH:6]2

Participants

8

Reactant 6

HCID 14812Phosphorus oxide (P4O10)HCID 24764HexamethyldisiloxaneHCID 663013,5-DimethoxyanilineHCID 516892Sodium BicarbonateHCID 16133246Trimethyl(phosphooxy)silaneHCID 18187381HCID 18187381, compound

Product 1

HCID 2794459HCID 2794459, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1.52 g (9.9 mmol) of 3,5-dimethoxyaniline and 2.30 g (12 mmol, 1.2 eq) of ethyl (α-formylphenylacetate are mixed together in a round-bottomed flask under a nitrogen atmosphere. The medium is stirred for 1 h at room temperature. A solution of trimethylsilyl polyphosphate (PPSE), freshly prepared from 4.56 g (0.03 mol) of P2O5, 10.9 ml (0.17 mol) of hexamethyldisiloxane and 50 ml of 1,2-dichloroethane, is added. The final mixture is maintained at 100° C. for 2 h. The heating is stopped and ice is then added to the reaction mixture. This mixture is then neutralized by addition of saturated sodium hydrogen carbonate solution (portionwise addition, exothermic reaction). The product is extracted with dichloromethane (large amount to be used). The organic phase is dried over MgSO4 and then evaporated under reduced pressure. The residue is taken up in ethyl acetate, which causes precipitation of the desired compound. The final product is isolated by filtration through a sinter funnel. After partial concentration of the filtrate, the final product reprecipitates. The solid is reisolated by filtration, this operation being repeated several times. Compound 34 (444 mg) is obtained in a yield of 16%.

Workup

  1. additionis added
  2. additionice is then added to the reaction mixture
  3. additionportionwise addition, exothermic reaction)
  4. extractionThe product is extracted with dichloromethane (large amount to be used)
  5. dry with materialThe organic phase is dried over MgSO4
  6. customevaporated under reduced pressure
  7. customprecipitation of the desired compound

Sources & evidence

ORD record
ord-f5ab0fcdffa147fc859aecee44ac17cc
Source dataset
uspto-grants-2003_07
Patent number
US06593342B1

Reaction notes

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