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

HRID 530057Notes

Reaction equation

HRID 530057 reaction equation
[CH2:1]([O:8][N:9]([C:11]1[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH3:20])[N:14]=[C:13]([NH:21][CH2:22][CH2:23][CH3:24])[N:12]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:25][S:26]([OH:29])(=[O:28])=[O:27]>>[S:26]([OH:29])([OH:28])(=[O:27])=[O:25].[CH2:1]([O:8][N:9]([C:11]1[N:12]=[C:13]([NH:21][CH2:22][CH2:23][CH3:24])[N:14]=[C:15]([NH:17][CH2:18][CH2:19][CH3:20])[N:16]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 57377806O-benzyl-N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-N-methyl-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-methyl-hydroxylamine (LIII) was reacted with 95% H2SO4 as described in Example 20 to yield O-benzyl-N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-N-methyl-hydroxylamine hydrogen sulfate (LIV) in quantitative yield. 400 MHz 1H NMR (DMSO-d6, ppm) 12.0-10.9 (1H, br s), 8.7-8.3 (1H, br s), 7.56-7.46 (2H, m), 7.46-7.37 (2.5H, m), 7.36-7.30 (0.5H, m), 5.07-4.95 (2H, m), 3.44-3.16 (7H, m), 1.61-1.45 (4H, m), 0.94-0.82 (6H, m). ESI-MS (m/z): 331 [M+H]+.

Sources & evidence

ORD record
ord-5c617a2f30234bd4b529f758877d40a5
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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