Nitrogen → HCID 86747832, compound

HRID 1721543Notes

Reaction equation

HRID 1721543 reaction equation
N#N.[OH:3][CH2:4][CH2:5][CH2:6][CH2:7][Si:8]([CH3:19])([CH3:18])[O:9][Si:10]([CH3:17])([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][OH:15].N1C=CC=CC=1.Cl[C:27]([O:29]C=C)=[O:28]>C(Cl)Cl.C(#N)C>[C:27](=[O:28])([OH:29])[O:15][CH:14]=[CH2:13].[OH:15][CH2:14][CH2:13][CH2:12][CH2:11][Si:10]([CH3:17])([CH3:16])[O:9][Si:8]([CH3:18])([CH3:19])[CH2:7][CH2:6][CH2:5][CH2:4][OH:3]

Participants

7

Reactant 4

HCID 947NitrogenHCID 1049PyridineHCID 78808Vinyl chloroformateHCID 27693461,3-Bis(4-hydroxybutyl)tetramethyldisiloxane

Product 1

HCID 86747832HCID 86747832, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 500 ml 3-neck, round bottom flask equipped with a reflux condenser, a mechanocal stirrer, a thermometer, a dropping funnel and a N2 blanket, is charged with 69.5 g (0.25 mole) of 1,3-bis(4-hydroxybutyl) tetramethyl disiloxane (Silar Lab.), pyridine, 19.5 g and 300 ml of methylene chloride. The contents are cooled down to between 0 and 5 degrees C. by an ice bath. Through the dropping funnel 25.3 g (0.25 mole) of vinyl chloroformate in 50 ml of methylene chloride is added dropwise into the flask at a rate such that the temperature is maintained between 0 and 5 degrees C. The contents are then stirred for another 4 hours and then passed through a silica gel column. The eluents are condensed and injected in 6-8 gram portions into a reverse phase high performance liquid chromatography unit (Waters), using acetonitrile as solvent. Three fractions are collected. The major (center) fraction from each injection is collected and condensed to give 1,3-bis(4-hydroxybutyl)tetramethyl disiloxane monovinyl carbonate. The monovinyl carbonate product (34.8 g or 0.1 mole) is charged into a flask as already described, along with 8.0 g of pyridine, 50 mg of hydroquinone and 200 ml of chloroform. The contents are cooled down to between 0 and 5 degrees C. Through a dropping funnel, 10.5 g (0.1 mole) of methacryloyl chloride in 50 ml of chloroform is added into the flask at such a rate that the temperature is maintained between 0 and 5 degrees C. The contents are stirred continuously for 4 hours and then passed through a silica gel column. The contents are then condensed and distilled under reduced pressure to give the named product. Hydroquinone (50 mg) is added into the named product.

Workup

  1. customA 500 ml 3-neck, round bottom flask equipped with a reflux condenser, a mechanocal stirrer
  2. temperatureThe contents are cooled down to between 0 and 5 degrees C
  3. temperatureis maintained between 0 and 5 degrees C
  4. customcondensed
  5. customThree fractions are collected
  6. customThe major (center) fraction from each injection is collected
  7. customcondensed

Sources & evidence

ORD record
ord-a9ddcb2a183a4e85bee893013626107e
Source dataset
uspto-grants-1996_04
Patent number
US05512205

Reaction notes

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