Cyanuric chloride → HCID 23313987, compound

HRID 1863360Notes

Reaction equation

HRID 1863360 reaction equation
Cl.[C:2]([NH:7][CH2:8][CH2:9][CH2:10][NH2:11])(=[O:6])[C:3]([CH3:5])=[CH2:4].[N:12]1[C:19]([Cl:20])=[N:18][C:16](Cl)=[N:15][C:13]=1[Cl:14].C(=O)(O)[O-].[Na+]>O.CC(C)=O>[C:2]([NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:16]1[N:18]=[C:19]([Cl:20])[N:12]=[C:13]([Cl:14])[N:15]=1)(=[O:6])[C:3]([CH3:5])=[CH2:4]

Participants

6

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 103750052-Propenamide, N-(3-aminopropyl)-2-methyl-, hydrochloride (1:1)

Product 1

HCID 23313987HCID 23313987, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of 71.6 g. (0.4 mole) of 3-methacrylamidopropylamine hydrochloride in 400 ml. of water being stirred at 0°-5° C. was added dropwise a solution of 79 g. (0.4 mole) of cyanuric chloride in 400 ml. of acetone. To this mixture was then added in portions 67.2 g. (0.8 mole) of sodium bicarbonate over the course of 1 hr. The mixture was stirred at room temperature for an additional hour and then 2 l of water was added. The product was collected by filtration and dried in vacuo at room temperature to yield 75.8 g. The product was recrystallized from 600 ml. of ethyl acetate to give 53.2 g. (46%) (mp 138°-140° C.).

Workup

  1. additionwas added dropwise a solution of 79 g
  2. additionTo this mixture was then added in portions 67.2 g
  3. customover the course of 1 hr
  4. filtrationThe product was collected by filtration
  5. customdried in vacuo at room temperature
  6. customto yield 75.8 g
  7. customThe product was recrystallized from 600 ml
  8. customof ethyl acetate to give 53.2 g

Sources & evidence

ORD record
ord-b0ba1f9f8e2f4b09bfef20cc987cac92
Source dataset
uspto-grants-1979_09
Patent number
US04168976

Reaction notes

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