Hydrochloric Acid → 2-(N'-(4-hydroxyphenyl)ureido)ethylmethacrylate

HRID 1070371Notes

Reaction equation

HRID 1070371 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[C:9]([O:14][CH2:15][CH2:16][N:17]=[C:18]=[O:19])(=[O:13])[C:10]([CH3:12])=[CH2:11].[N-]=C=O.Cl>O.CN(C)C(=O)C>[C:9]([O:14][CH2:15][CH2:16][NH:17][C:18]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:1]=1)=[O:19])(=[O:13])[C:10]([CH3:12])=[CH2:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 354092-Isocyanatoethyl methacrylateHCID 105034Isocyanate

Product 1

HCID 228923762-(N'-(4-hydroxyphenyl)ureido)ethylmethacrylateYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Into a 1 liter fask 500 g of N,N-Dimethyl acetamide and 173.5 g (1.6 mole) of p-aminophenol were added. This mixture was placed in cold bath and 234.9 g (1.5 mole) of methacryloyl oxyethyl isocyanate was added over a period of 1 hour. After the addition was complete, stirring was continued for 5 hours at room temperature. The mixture was tested for isocyanate functionality using IR spectroscopy. 30 ml of concentrated HCl was added to the mixture and was stirred for 15 minutes. The mixture was poured into 4.5 liter of water. The deposit was filtered, washed and dried to produce 370 g of 2-(N′-(4-hydroxyphenyl)ureido)ethyl methacrylate.

Workup

  1. customThis mixture was placed in cold bath
  2. additionAfter the addition
  3. stirringwas stirred for 15 minutes
  4. filtrationThe deposit was filtered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-6b78b2288e58467b9dc04b0bfa0cbd18
Source dataset
uspto-grants-2005_06
Patent number
US06902860B2

Reaction notes

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