Sulfuric Acid → HCID 86665990, compound

HRID 1752141Notes

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]([CH3:19])[O:16][CH2:17][CH3:18])[N:6]=1)[CH2:2][CH3:3].[OH:20][S:21]([OH:24])(=[O:23])=[O:22]>>[S:21]([OH:24])([OH:23])(=[O:22])=[O:20].[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]([CH3:19])[O:16][CH2:17][CH3:18])[N:6]=1)[CH2:2][CH3:3]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 57378017HCID 57378017, compound

Product 1

HCID 86665990HCID 86665990, compoundYield 91%

Procedure

N-(4,6-bis-n-propylamino-[1,3,5]triazin-2-yl)-O-ethyl-N-methyl-hydroxylamine (XCVI) was reacted with 95% H2SO4 as described in Example 20, to afford (XCVII) in 91% yield. 400 MHz 1H NMR (DMSO-d6, ppm) 11.7-10.8 (1H, br s), 8.79-7.34 (2H, m), 4.09-3.98 (2H, m), 3.40-3.20 (7H, m), 1.61-1.46 9 (4H, m), 1.27 (3H, t, J=7.1 Hz), 0.94-0.84 (6H, m). 400 MHz 1HNMR (D2O, ppm) 3.99-3.88 (2H, m), 3.34-3.13 (7H, m), 1.52-1.39 (4H, m), 1.14 (3H, t, J=7.1 Hz), 0.76 (6H, t, J=7.5 Hz). ESI-MS (m/z): 269 [M+H]+. M.P.: 84-86° C.

Workup

customto afford (XCVII) in 91% yield

Sources & evidence

ORD record: ord-cb62aff120434293b45f2d814a33d2dc
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162992B2

Reaction notes

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