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

HRID 530069Notes

Reaction equation

HRID 530069 reaction equation
[CH2:1]([O:8][N:9]([C:12]1[N:17]=[C:16]([NH:18][CH2:19][CH2:20][CH3:21])[N:15]=[C:14]([NH:22][CH2:23][CH2:24][CH3:25])[N:13]=1)[CH2:10]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:26][S:27]([OH:30])(=[O:29])=[O:28]>>[S:27]([OH:30])([OH:29])(=[O:28])=[O:26].[CH2:1]([O:8][N:9]([C:12]1[N:13]=[C:14]([NH:22][CH2:23][CH2:24][CH3:25])[N:15]=[C:16]([NH:18][CH2:19][CH2:20][CH3:21])[N:17]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 57377910O-benzyl-N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-N-ethyl-hydroxylamine

Product 1

HCID 86665976O-benzyl-N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-N-methyl-hydroxylamine hydrogen sulfate

Procedure

O-Benzyl-N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-N-ethyl-hydroxylamine (LXVIII) was reacted with 95% H2SO4 as described in Example 9 to yield O-benzyl-N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-N-methyl-hydroxylamine hydrogen sulfate (LXIX) in quantitative yield. 400 MHz 1H NMR (DMSO-d6, ppm) 12.0-11.0 (1H, br s), 8.7-8.0 (1H, m), 7.57-7.30 (5H, m), 5.07-4.95 (2H, m), 3.89-3.68 (2H, m), 3.39-3.14 (4H, m), 1.63-1.42 (4H, m), 1.23-1.07 (3H, m), 0.94-0.77 (6H, m). ESI-MS (m/z): 345 [M+H]+.

Sources & evidence

ORD record
ord-c47bd244f7fd4fb7b419c35ebaab21da
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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