Phenyl isocyanate → 2-[(Phenylcarbamoyl)oxy]ethyl prop-2-enoate

HRID 1514836Notes

Reaction equation

C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.CN(CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1)C.[C:41]1([N:47]=[C:48]=[O:49])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[C:50]([O:54][CH2:55][CH2:56][OH:57])(=[O:53])[CH:51]=[CH2:52].[N-]=C=O>>[C:50]([O:54][CH2:55][CH2:56][O:57][C:48](=[O:49])[NH:47][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(=[O:53])[CH:51]=[CH2:52]

Participants

Reactant 5

HCID 7672Phenyl isocyanate

HCID 131652-Hydroxyethyl acrylate

HCID 314042,6-Di-tert-butyl-4-methylphenol

HCID 85160N,N',N''-Tris(3-dimethylaminopropyl)hexahydro-S-triazine

HCID 105034Isocyanate

Product 1

HCID 214639092-[(Phenylcarbamoyl)oxy]ethyl prop-2-enoate

Conditions

Temperature: 60 °C

Procedure

0.25 g of 2,6-di-tert-butyl-4-methylphenol, 0.12 g of Desmorapid Z, 126.4 g of phenyl isocyanate were initially introduced into a 500 ml round-bottomed flask and heated to 60° C. Thereafter, 123.3 g of 2-hydroxyethyl acrylate were added dropwise and the mixture was kept further at 60° C. until the isocyanate content had fallen below 0.1%. Cooling was then effected. The product was obtained as a crystalline solid (preparation described in DE 2329142).

Workup

temperatureCooling
customThe product was obtained as a crystalline solid (preparation described in DE 2329142)

Sources & evidence

ORD record: ord-91083c9c77914509b029d5838ebc415e
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222314B2

Reaction notes

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