Sulfuric Acid → N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-isopropyl-N-methyl-hydroxylamine hydrogen sulfate

HRID 530065Notes

Reaction equation

HRID 530065 reaction equation
[CH2:1]([NH:4][C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH3:14])[N:8]=[C:7]([N:15]([CH3:20])[O:16][CH:17]([CH3:19])[CH3:18])[N:6]=1)[CH2:2][CH3:3].[OH:21][S:22]([OH:25])(=[O:24])=[O:23]>O1CCOCC1>[S:22]([OH:25])([OH:24])(=[O:23])=[O:21].[CH2:1]([NH:4][C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH3:14])[N:8]=[C:7]([N:15]([CH3:20])[O:16][CH:17]([CH3:18])[CH3:19])[N:6]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 57377909N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-isopropyl-N-methyl-hydroxylamine

Product 1

HCID 86665981N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-isopropyl-N-methyl-hydroxylamine hydrogen sulfate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-isopropyl-N-methyl-hydroxylamine (LXIV, 1.93 g, 6.83 mmol) in 1,4-dioxane (6 mL) at 0° C. was added 95% H2SO4 (0.36 mL, 6.83 mmol) in a drop-wise manner. The mixture was stirred for 0.5 h at room temperature and then the 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)-O-isopropyl-N-methyl-hydroxylamine hydrogen sulfate (quantitative yield). 400 MHz 1H-NMR (DMSO-d6, ppm) 11.3-10.7 (1H, br s), 8.8-8.4 (1H, br s), 8.2-8.0 (0.3H, br s), 8.04-7.65 (0.7H, m), 4.43-4.28 (1H, m), 3.42-3.18 (7H, m), 1.64-1.44 (4H, m), 1.25 (6H, d, J=6.1 Hz), 0.94-0.82 (6H, m). ESI-MS (m/z): 283 [M+H]+.

Workup

  1. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-42f5192c261d43fbb0254568ed7d4edc
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

Loading…