2-Isocyanatoethyl methacrylate → HCID 57567229, compound

HRID 1727335Notes

Reaction equation

HRID 1727335 reaction equation
[OH:1][CH:2]1[CH2:9][S:8][CH2:7][CH2:6][CH2:5][S:4][CH2:3]1.[C:10]([O:15][CH2:16][CH2:17][N:18]=[C:19]=[O:20])(=[O:14])[C:11]([CH3:13])=[CH2:12]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.O1CCCC1>[S:4]1[CH2:5][CH2:6][CH2:7][S:8][CH2:9][CH:2]([O:1][C:19]([NH:18][CH2:17][CH2:16][O:15][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12])=[O:20])[CH2:3]1

Participants

5

Reactant 2

HCID 354092-Isocyanatoethyl methacrylateHCID 8545011,5-Dithiocan-3-ol

Product 1

HCID 57567229HCID 57567229, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-hydroxy-1,5-dithiacyclooctane (5.00 grams, 30 millimoles), 2-isocyanatoethyl methacrylate (4.72 grams, 30 millimoles), tetrahydrofuran (15 milliliters), and one drop of dibutyltin dilaurate were stirred at 55° C. for three hours. The solvent was then removed under reduced pressure and the crude product was purified by column chromatography over silica gel using a mixture of ethyl acetate/hexane (30/70). The product was isolated as a white solid (7.72 grams, 79% yield). Purity and structure verification of Example 9 were confirmed by 1H NMR.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe crude product was purified by column chromatography over silica gel using
  3. additiona mixture of ethyl acetate/hexane (30/70)

Sources & evidence

ORD record
ord-e8935d5007d34588891e2b45bfcd27f9
Source dataset
uspto-grants-2009_02
Patent number
US07495054B2

Reaction notes

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