Phenothiazine → Bis(trimethylsilyl)methylacrylate

HRID 1278529Notes

Reaction equation

HRID 1278529 reaction equation
[CH3:1][Si:2]([CH:5]([Si:7]([CH3:10])([CH3:9])[CH3:8])Cl)([CH3:4])[CH3:3].[C:11]([O-:15])(=[O:14])[CH:12]=[CH2:13].[Na+].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(#N)CCC>[CH3:1][Si:2]([CH:5]([O:15][C:11](=[O:14])[CH:12]=[CH2:13])[Si:7]([CH3:10])([CH3:9])[CH3:8])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 7108PhenothiazineHCID 552583Bis(trimethylsilyl)chloromethaneHCID 4068533Sodium acrylate

Product 1

HCID 18764809Bis(trimethylsilyl)methylacrylate

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 8008ButyronitrileSolvent

Procedure

Bis(trimethylsilyl)chloromethane (Aldrich) 39 g, 0.2 mole), sodium acrylate (28 g, 0.3 mole), Adogen 464 (Aldrich) (6.96 g), and phenothiazine (0.10 grams) were placed in a round bottom flask equipped with a condenser, mechanical stirrer and a nitrogen inlet. The flask was charged with 100 ml of butyronitrile and heated to reflux while stirring. After 6 hours, the mixture was diluted with 150 ml hexanes and filtered to remove the solids. The solvents were removed under reduced pressure. Fractional distillation of the residue under reduced pressure gave 35.5 grams 975%) of the desired product at 45-58° C. at 0.5 mm pressure.

Workup

  1. customequipped with a condenser, mechanical stirrer and a nitrogen inlet
  2. temperatureheated
  3. temperatureto reflux
  4. filtrationfiltered
  5. customto remove the solids
  6. customThe solvents were removed under reduced pressure
  7. distillationFractional distillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-3901f3841ab847a79d34516e6d4156e3
Source dataset
uspto-grants-2002_09
Patent number
US06444408B1

Reaction notes

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