Melamine → HCID 15597651, compound

HRID 381657Notes

Reaction equation

HRID 381657 reaction equation
[N:1]1[C:8]([NH2:9])=[N:7][C:5]([NH2:6])=[N:4][C:2]=1[NH2:3].[H][H].[CH2:12]([OH:18])[CH2:13][O:14][CH2:15][CH2:16]O>[Pd]>[NH2:3][C:2]1[N:4]=[C:5]([NH2:6])[N:7]=[C:8]([NH:9][CH2:16][CH2:15][O:14][CH2:13][CH2:12][OH:18])[N:1]=1.[NH2:3][C:2]1[N:4]=[C:5]([NH:6][CH2:16][CH2:15][O:14][CH2:13][CH2:12][OH:18])[N:7]=[C:8]([NH:9][CH2:16][CH2:15][O:14][CH2:13][CH2:12][OH:18])[N:1]=1

Participants

6

Reactant 3

HCID 7955Melamine2×HCID 8117Diethylene GlycolHCID 178418361HCID 178418361, compound

Product 2

HCID 15597651HCID 15597651, compoundHCID 155976522-{2-[(4,6-Diamino-1,3,5-triazin-2-yl)amino]ethoxy}ethan-1-ol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a stainless steel autoclave of an inner volume of 100 ml, 1.26 g (10 mmol) of melamine, 250 mg of 5% Pd—C catalyst (50% hydrated preparation), 250 mg of CuO—Cr2O3—NiO—BaO catalyst (T-4364, manufactured by Nissan Girdler Catalyst Co., Ltd.), and 30 ml of diethylene glycol were charged. After the inside of the system was sufficiently substituted with nitrogen gas, 10 kg/cm2 of hydrogen gas was introduced at normal temperature under pressure. Then, the temperature was elevated while stirring, and after the temperature reached 260° C., the reaction was carried out at the same temperature for further 2 hours. After cooling, the reaction mixture was taken out and quantitative analysis of the reaction product was performed under the above analytical conditions. As a result, the reaction conversion rate of the starting material melamine was 50.0% and it was confirmed that there were produced 2,4-diamino-6-(5-hydroxy-3-oxapentylamino)-1,3,5-triazine in a yield of 34.3% and 2-amino-4,6-bis(5-hydroxy-3-oxapentylamino)-1,3,5-triazine in a yield of 6.7%, respectively.

Workup

  1. additionwas introduced at normal temperature under pressure
  2. customreached 260° C.
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-050d7c6431fd4b3e9e1137d92d104818
Source dataset
uspto-grants-2001_10
Patent number
US06307046B1

Reaction notes

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