Pyridine → HCID 20431430, compound

HRID 1263067

Reaction equation

HRID 1263067 reaction equation
[C:1]([NH:6][CH2:7][C:8]([OH:10])=O)(=[O:5])[C:2]([CH3:4])=[CH2:3].Cl.[NH2:12][C:13]1[C:18]([OH:19])=[C:17]([Cl:20])[C:16]([CH3:21])=[C:15]([Cl:22])[CH:14]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>O.C(OCC)(=O)C>[C:1]([NH:6][CH2:7][C:8]([NH:12][C:13]1[C:18]([OH:19])=[C:17]([Cl:20])[C:16]([CH3:21])=[C:15]([Cl:22])[CH:14]=1)=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 152645N-Methacryloyl glycineHCID 1702236-Amino-2,4-dichloro-m-cresol hydrochloride

Product 1

HCID 20431430HCID 20431430, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To mixture composed of 68 g (0.48 mol) of N-methacryloyl glycine obtained in the above described manner and 46 g (0.2 mol) of 6-amino-2,4-dichloro-3-methylphenol hydrochloride were added 114 ml (1.44 mol) of pyridine and 1 liter of ethyl acetate and stirred under cooling. To the solution was added dropwise 29 ml (0.4 mol) of thionyl chloride. After the completion of the reaction, 300 ml of water was added to the reaction solution and extracted with ethyl acetate. The ethyl acetate solution was concentrated and to the residue was added acetonitrile. The crystals thus deposited were collected and recrystallized from acetonitrile to obtain 34.8 g of Monomer Coupler (2).

Workup

  1. customobtained in the
  2. temperatureunder cooling
  3. additionwas added to the reaction solution
  4. extractionextracted with ethyl acetate
  5. concentrationThe ethyl acetate solution was concentrated and to the residue
  6. additionwas added acetonitrile
  7. customThe crystals thus deposited were collected
  8. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-e138b3a795bc487b9dda14d35b363ac0
Source dataset
uspto-grants-1984_06
Patent number
US04455366

Linked notes

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