Pyridine → HCID 20431432, compound

HRID 2413016Notes

Reaction equation

HRID 2413016 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:20])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[OH:19])=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O.[C:36](Cl)(=[O:40])[C:37]([CH3:39])=[CH2:38]>O.C(#N)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:20])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:36](=[O:40])[C:37]([CH3:39])=[CH2:38])=[CH:14][C:13]=2[OH:19])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7416NitrobenzeneHCID 13528Methacryloyl chlorideHCID 14548764N-(4-Amino-2-hydroxyphenyl)-N'-(4-cyanophenyl)urea

Product 1

HCID 20431432HCID 20431432, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

10.8 g (0.04 mol) of 2-(4-cyanophenylureido)-5-aminophenol was added to 100 ml of acetonitrile and to which were added 17.6 ml (0.2 mol) of pyridine and 0.3 ml of nitrobenzene while cooling with stirring. To the solution was added dropwise 5.0 g (0.048 mol) of methacrylic chloride and the mixture was stirred for about 1.5 hours. 200 ml of water was added to the reaction mixture and the crystals thus deposited were collected by filtration and recrystallized from acetone to obtain 3.8 g (28.3%) of Monomer Coupler (18).

Workup

  1. temperaturewhile cooling
  2. stirringthe mixture was stirred for about 1.5 hours
  3. filtrationthe crystals thus deposited were collected by filtration
  4. customrecrystallized from acetone

Sources & evidence

ORD record
ord-96a343744e9f41558f5a00ea932cee52
Source dataset
uspto-grants-1985_01
Patent number
US04495272

Reaction notes

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