Methacryloyl isocyanate → HCID 19801065, compound

HRID 1646635Notes

Reaction equation

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

Participants

Reactant 2

HCID 10942374Methacryloyl isocyanate

HCID 198010732-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-chloromethyl-1,4-cyclohexanediol

Product 1

HCID 19801065HCID 19801065, compoundYield 34.1%

Procedure

As in Example 2, a mixture of 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-chloromethyl-1,4-cyclohexanediol (1.13 g) and methacryloylisocyanate (800 mg) was stirred for 30 minutes at room temperatures. The reaction mixture was purified by means of a silica gel column chromatography (carrier 50 g, developing solvent:hexane-ethyl acetate=3:1) to afford 4-O-(methacryloylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-chloromethyl-1,4-cyclohexanediol (520 mg, yield 34%) as colorless crystals.

Workup

customThe reaction mixture was purified by means of a silica gel column chromatography (carrier 50 g, developing solvent:hexane-ethyl acetate=3:1)

Sources & evidence

ORD record: ord-30c0bc38fab1472a85b5a6549bf405ce
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180735

Reaction notes

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