2-Isocyanatoethyl methacrylate → HCID 89629922, compound

HRID 578608Notes

Reaction equation

HRID 578608 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH:10]([CH2:20][OH:21])[CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[N:22]([CH2:25][CH2:26][O:27][C:28](=[O:32])[C:29]([CH3:31])=[CH2:30])=[C:23]=[O:24]>ClCCl.[Sn]>[CH2:14]([O:13][P:12]([CH2:11][CH:10]([CH2:20][O:21][C:23](=[O:24])[NH:22][CH2:25][CH2:26][O:27][C:28](=[O:32])[C:29]([CH3:31])=[CH2:30])[CH2:9][P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])(=[O:19])[O:16][CH2:17][CH3:18])[CH3:15]

Participants

5

Reactant 2

HCID 354092-Isocyanatoethyl methacrylateHCID 11759759HCID 11759759, compound

Product 1

HCID 89629922HCID 89629922, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 5352426Tin atomCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-hydroxymethyl-1,3-propylene-bisphosphonic acid tetraethylester (4.8 g, 13.8 mmol) in anhydrous dichloromethane (6.0 ml) was added to a 1% solution of the tin catalyst Metatin 712 in anhydrous dichloromethane (4.0 ml). Then isocyanatoethyl-methacrylate (1.96 ml, 13.8 mmol) was added dropwise, and the reaction mixture was stirred for 3 h at room temperature. After concentrating in vacuo the obtained crude product was purified by column chromatography (eluent: ethyl acetate/methanol 95:5). 6.0 g (86% yield) of the product was obtained as a colorless oil.

Workup

  1. concentrationAfter concentrating in vacuo the
  2. customobtained crude product
  3. customwas purified by column chromatography (eluent: ethyl acetate/methanol 95:5)

Sources & evidence

ORD record
ord-435ec8131f244a87be4dbeca167dee3c
Source dataset
uspto-grants-2015_05
Patent number
US09040602B2

Reaction notes

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