Cyanuric chloride → HCID 57314960, compound

HRID 1252235Notes

Reaction equation

HRID 1252235 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[OH:10][CH2:11][CH2:12][O:13][C:14](=[O:28])[NH:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][NH:21][C:22](=[O:27])[O:23][CH2:24][CH2:25][OH:26]>CC(C)=O.O>[OH:10][CH2:11][CH2:12][O:13][C:14]([NH:15][CH2:16][CH2:17][N:18]([C:8]1[N:1]=[C:2]([N:18]([CH2:17][CH2:16][NH:15][C:14]([O:13][CH2:12][CH2:11][OH:10])=[O:28])[CH2:19][CH2:20][NH:21][C:22]([O:23][CH2:24][CH2:25][OH:26])=[O:27])[N:4]=[C:5]([Cl:6])[N:7]=1)[CH2:19][CH2:20][NH:21][C:22]([O:23][CH2:24][CH2:25][OH:26])=[O:27])=[O:28]

Participants

5

Reactant 2

HCID 7954Cyanuric chloride2×HCID 14533831HCID 14533831, compound3×

Product 1

HCID 57314960HCID 57314960, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To 50 g water in a 3-neck flask equipped with stirrer and a thermometer, were added 9.2 g (0.05 m) of cyanuric chloride, dissolved in 50 g acetone below 10° C. To the white slurry of cyanuric chloride, 27.9 g of bis(2-hydroxyethyl)(iminodiethylene)biscarbamate (HEC), NH(CH2CH2NHCO2CH2CH2OH)2 dissolved in 50 g of water was added over a period of 15 minutes. During the addition, the reaction temperature was maintained below 12° C. After complete addition of HEC, the slurry turned into a clear solution. To this was added 10% caustic to maintain the reaction pH at about 7 and the reaction mixture was allowed to warm up to 25° C. At 25° C., as the reaction progressed, a white crystalline solid slowly separated out. After 4 hrs. at 25°-35° C., the solids were separated by filtration, washed with water and recrystallized from ethanol. The product yield was 24 g and m.p. 174° C. The structure of the product was confirmed by nuclear magnetic resonance (nmr) and fast atomic bombardment (fab), mass spectrometry to be that of FORMULA I: ##STR20##

Workup

  1. additionwas added over a period of 15 minutes
  2. additionDuring the addition
  3. temperaturethe reaction temperature was maintained below 12° C
  4. additionTo this was added 10%
  5. temperatureto maintain the reaction pH at about 7
  6. customAt 25° C.
  7. customa white crystalline solid slowly separated out
  8. customat 25°-35° C., the solids were separated by filtration
  9. washwashed with water
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-539b342d9d5f41608bb63be031e0d793
Source dataset
uspto-grants-1988_05
Patent number
US04742118

Reaction notes

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