Dicyandiamide → 1,3,5-Triazine-2,4-diamine, 6,6',6''-(1,3,6-hexanetriyl)tris-

HRID 1112475Notes

Reaction equation

[C:1]([CH2:3][CH2:4][CH:5]([C:11]#[N:12])[CH2:6][CH2:7][CH2:8][C:9]#[N:10])#[N:2].[C:13]([N:15]=[C:16]([NH2:18])[NH2:17])#[N:14].C[O-].[Na+]>CS(C)=O>[NH2:14][C:13]1[N:15]=[C:16]([NH2:18])[N:17]=[C:1]([CH2:3][CH2:4][CH:5]([C:11]2[N:17]=[C:16]([NH2:18])[N:15]=[C:13]([NH2:14])[N:12]=2)[CH2:6][CH2:7][CH2:8][C:9]2[N:17]=[C:16]([NH2:18])[N:15]=[C:13]([NH2:14])[N:10]=2)[N:2]=1

Participants

Conditions

Temperature: 130 °C

Procedure

161 g (1 mole) of 1,3,6-tricyanohexane and 277.2 g (3.3 moles) of dicyandiamide were added to 750 g of dimethyl sulfoxide as the reaction medium, followed by further addition of 68 g (1 mole) of sodium methylate as the catalyst. The mixture was stirred under heating at 130° C for 3 hours in a nitrogen atmosphere. After completion of the reaction the reaction mixture was cooled to 25° C to precipitate the reaction product, followed by separating the crude reaction product by filtration. Purification was conducted by dissolving the crude product in excess amount of dimethyl sulfoxide at 135° C and then precipitating the product by cooling. After repeating this procedure 5 times, 292 g of 1,3,6-tris(4,6-diamino-1,3,5-triazine-2-yl)hexane as a white powder were obtained.

Workup

customAfter completion of the reaction the reaction mixture
temperaturewas cooled to 25° C
customto precipitate the reaction product
customby separating the crude
customreaction product
filtrationby filtration
customPurification
dissolutionby dissolving the crude product in excess amount of dimethyl sulfoxide at 135° C
customprecipitating the product
temperatureby cooling

Sources & evidence

ORD record: ord-b72da1a880c546d7b6aed4049554069e
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04122269

Reaction notes

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