Diglycolamine → 2-{2-[(4,6-Diamino-1,3,5-triazin-2-yl)amino]ethoxy}ethan-1-ol

HRID 365712Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4](Cl)[N:3]=1.[NH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16].[OH-].[Na+]>O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16])[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

14.5 g (0.1 mol) of 2,4-diamino-6-chloro-1,3,5-triazine and 11.6 g (0.11 mol) of 2-(2'-aminoethoxy)ethanol were added to 60 mL of water and heated to 100° C. while stirring the mixture as a suspension. After continuing the reaction for 2 hours, an aqueous solution of 4.0 g (0.1 mol) of sodium hydroxide in 20 mL of water was dropwise added over 1 hour while maintaining the reaction temperature, and the reaction was continued for further 3 hours at the same temperature. The homogeneous reaction mixture thus obtained was gradually cooled and allowed to stand at room temperature for one night. The crystals precipitated were collected by filtration, washed with a small amount of water, and recrystallized from water to obtain 13.5 g of the intended compound, 2,4-diamino-6-(5-hydroxy-3-oxapentylamino)-1,3,5-triazine as crystals. Yield 62%.

Workup

customthe reaction for 2 hours
temperaturewhile maintaining the reaction temperature
customThe homogeneous reaction mixture thus obtained
temperaturewas gradually cooled
waitto stand at room temperature for one night
customThe crystals precipitated
filtrationwere collected by filtration
washwashed with a small amount of water
customrecrystallized from water

Sources & evidence

ORD record: ord-c34992e282524a64a43e3dd7a338a233
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127538

Reaction notes

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