Ethanol → Carbamic acid, ethenyl-, methyl ester

HRID 2253931Notes

Reaction equation

HRID 2253931 reaction equation
[C:1](=[O:4])([OH:3])[OH:2].[C:5](#[N:8])[CH:6]=[CH2:7].C[OH:10].[CH2:11]([OH:13])[CH3:12]>>[CH:5]([NH:8][C:1](=[O:4])[O:2][CH3:11])=[CH2:6].[C:5]([NH:8][O:3][C:1]([O:13][CH2:11][CH3:12])=[O:2])(=[O:10])[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 887MethanolHCID 87075430HCID 87075430, compound

Product 2

HCID 10866270Carbamic acid, ethenyl-, methyl esterHCID 131718045HCID 131718045, compound

Procedure

U.S. Pat. No. 3,715,385, Wolgemuth, et al. (1973) describes still another method of obtaining N-vinyl carbamic acid esters by condensation-re-arrangement of acrylonitrile carbonate with methanol or ethanol. In Example I, methyl (N-vinyl carbamate) was obtained in 40% yield from carboethoxy acrylohydroxamate at 100° C. using a sodium alkoxy tin catalyst. The carboethoxy acrylohydroxamate is said to decompose at reaction temperature to yield acrylonitrile carbonate.

Sources & evidence

ORD record
ord-a8fada51851e47ac8d15fda088616dfe
Source dataset
uspto-grants-1993_08
Patent number
US05233077

Reaction notes

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