Melamine → HCID 131718351, compound

HRID 2399771Notes

Reaction equation

HRID 2399771 reaction equation
[N:1]1[C:8]([NH2:9])=[N:7][C:5]([NH2:6])=[N:4][C:2]=1[NH2:3].[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([N:22]=[C:23]=[O:24])([CH3:21])[CH3:20])[CH:14]=1)=[CH2:12]>CS(C)=O>[CH3:12][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([N:22]=[C:23]=[O:24])([CH3:20])[CH3:21])[CH:14]=1)=[CH2:10].[N:1]1[C:8]([NH2:9])=[N:7][C:5]([NH2:6])=[N:4][C:2]=1[NH2:3]

Participants

4

Reactant 2

HCID 7955MelamineHCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

Product 1

HCID 131718351HCID 131718351, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

In a 2 liter three neck glass reactor equipped with agitator, thermometer, reflux condenser, nitrogen inlet and dropping funnel, 252 g (2 moles) of melamine was dispersed in 800 ml of DMSO (dimethylsulfoxide) under vigorous agitation. A solution of 423 g (2.1 moles) of m-TMI in 200 ml DMSO was added to the slurry at 110°-113° C. in 3.5 hours. The reaction temperature was maintained for an additional hour. To maintain effective agitation, the thickening slurry was diluted several times during the reaction with a total of 150 ml of DMSO. After cooling to ambient temperature, the reaction mixture was filtered, the white solid was rinsed on a filter with THF (tetrahydrofuran) and reslurried in 800 ml of THF. After agitation at 64° C. for 80 minutes, the product was filtered, rinsed on the filter with THF and dried first in a hot air circulation oven at 60° C. overnight (16 hours), then in a vacuum oven (full pump vacuum) at 90°- 100° C. for 4 hours. The yield of the white solid product was 665 g. From the first flitrate 85 g and from the second (wash) 73 g of white solids were recovered. Infrared (IR) and Thermal Gravimetric Analysis (TGA) indicated that these products still contained 15-20% of DMSO.

Workup

  1. temperaturethermometer, reflux condenser, nitrogen inlet
  2. temperatureThe reaction temperature was maintained for an additional hour
  3. temperatureTo maintain effective agitation
  4. additionthe thickening slurry was diluted several times
  5. filtrationthe reaction mixture was filtered
  6. washthe white solid was rinsed on
  7. filtrationa filter with THF (tetrahydrofuran)
  8. filtrationthe product was filtered
  9. washrinsed on the
  10. filtrationfilter with THF
  11. customdried first in a hot air circulation oven at 60° C. overnight (16 hours)
  12. waitin a vacuum oven (full pump vacuum) at 90°- 100° C. for 4 hours
  13. washFrom the first flitrate 85 g and from the second (wash) 73 g of white solids
  14. customwere recovered

Sources & evidence

ORD record
ord-b6d1d82db2d348c191497b93e58a7f0a
Source dataset
uspto-grants-1995_09
Patent number
US05451638

Reaction notes

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