Sulfuric Acid → N-(4,6-Bis-propylamino-[1,3,5]triazin-2-yl)-N,N'-dimethyl-hydrazine hydrogen sulfate

HRID 530053Notes

Reaction equation

HRID 530053 reaction equation
[OH:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][N:7]([C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[N:13]=[C:12]([NH:20][CH2:21][CH2:22][CH3:23])[N:11]=1)[NH:8][CH3:9]>O1CCOCC1>[S:2]([OH:5])([OH:4])(=[O:3])=[O:1].[CH2:17]([NH:16][C:14]1[N:13]=[C:12]([NH:20][CH2:21][CH2:22][CH3:23])[N:11]=[C:10]([N:7]([CH3:6])[NH:8][CH3:9])[N:15]=1)[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 573781346-(N,N'-dimethyl-hydrazino)-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 67773335N-(4,6-Bis-propylamino-[1,3,5]triazin-2-yl)-N,N'-dimethyl-hydrazine hydrogen sulfate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

95% H2SO4 (0.26 mL, 4.62 mmol) was added dropwise to the solution of 6-(N,N′-dimethyl-hydrazino)-N,N′-dipropyl-[1,3,5]triazine-2,4-diamine (XLIX) (1.17 g, 4.62 mmol) in 1,4-dioxane (10 mL) at 0° C. The mixture was stirred for 0.5 h at room temperature; volatiles were removed under reduced pressure. The residue was co-evaporated with dry toluene (3×25 mL) to yield N-(4,6-Bis-propylamino-[1,3,5]triazin-2-yl)-N,N′-dimethyl-hydrazine hydrogen sulfate (L) in quantitative yield. 400 MHz 1H NMR (DMSO-d6, ppm) 8.48-8.32 (1H, m), 7.9-7.7 (0.5H, br s), 7.70-7.61 (0.5H, m), 3.34-3.20 (4H, m), 3.21 (1.5H, s), 3.17 (1.5H, s), 2.52 (1.5H, s), 2.51 (1.5H, s, overlapped with DMSO), 1.59-1.46 (4H, m), 0.93-0.82 (6H, m). ESI-MS (m/z): 254 [M+H]+.

Workup

  1. customvolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-f4ad1f7e904d4cfbabe91ba044f74558
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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