Sulfuric Acid → 1380342-00-6

HRID 530041Notes

Reaction equation

HRID 530041 reaction equation
[OH:1][S:2]([OH:5])(=[O:4])=[O:3].[CH2:6]([NH:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[N:13]=[C:12]([N:20]([CH3:23])[O:21][CH3:22])[N:11]=1)[CH2:7][CH3:8]>O1CCOCC1>[CH2:6]([NH:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[N:13]=[C:12]([N:20]([CH3:23])[O:21][CH3:22])[N:11]=1)[CH2:7][CH3:8].[S:2]([OH:5])([OH:4])(=[O:3])=[O:1].[CH2:6]([NH:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][CH2:18][CH3:19])[N:13]=[C:12]([N:20]([CH3:23])[O:21][CH3:22])[N:11]=1)[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 57340959N-(4,6-Bis(propylamino)-1,3,5-triazin-2-yl)-N,O-dimethylhydroxylamine

Product 2

HCID 57340959N-(4,6-Bis(propylamino)-1,3,5-triazin-2-yl)-N,O-dimethylhydroxylamineHCID 866659731380342-00-6Yield 171.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Concentrated (95%) H2SO4 (0.72 mL, 12.74 mmol) was added in a dropwise manner to a solution of N-(4,6-bis-n-propylamino-[1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine (XXXV, 3.24 g, 12.74 mmol) in 1,4-dioxane (100 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). The resulting white residue was crystallized from ethanol/ethyl ether to yield N-(4,6-bis-n-propylamino-[1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine, hydrogen sulfate (XXXVI, 3.86 g, 86% yield) as a white solid. 1H NMR (400 MHz, DMSO): δ (ppm) 12.0-11.2 (1H, br s), 8.7-8.3 (0.7H, br s), 8.10 (0.3H, br s), 7.8-7.3 (1H, m), 3.78 (3H, s), 3.40-3.20 (7H, m), 1.61-1.45 (4H, m), 0.93-0.84 (6H, m). ESI-MS (m/z) 255 [M+H]+; melting point: 134-135° C.

Workup

  1. customvolatiles were removed under reduced pressure
  2. customThe resulting white residue was crystallized from ethanol/ethyl ether

Sources & evidence

ORD record
ord-8bd54548b4704beea8d5d0273cb47c23
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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