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

HRID 2204932Notes

Reaction equation

HRID 2204932 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

6

Reactant 5

HCID 7672Phenyl isocyanateHCID 131652-Hydroxyethyl acrylateHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 85160N,N',N''-Tris(3-dimethylaminopropyl)hexahydro-S-triazineHCID 105034Isocyanate

Product 1

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

Conditions

Temperature
60 °C

Procedure

A 500 ml round-bottom flask was initially charged with 0.25 g of 2,6-di-tert-butyl-4-methylphenol, 0.12 g of Desmorapid Z and 126.4 g of phenyl isocyanate, and the mixture was heated to 60° C. Subsequently, 123.3 g of 2-hydroxyethyl acrylate were added dropwise and the mixture was kept at 60° C. until the isocyanate content had fallen below 0.1%. This was followed by cooling. The product was obtained as a crystalline solid (preparation described in DE 2329142). The product has a melting point of 66-68° C. (Bowman, Macromolecules, 2004, 37 (11), 4062-4069).

Workup

  1. temperatureby cooling
  2. customThe product was obtained as a crystalline solid (preparation described in DE 2329142)

Sources & evidence

ORD record
ord-33d5930390e5453d9282cb80f1bacd39
Source dataset
uspto-grants-2016_06
Patent number
US09366957B2

Reaction notes

Loading…