Sulfuric Acid → 6-[1,2]Oxazinan-2-yl-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine hydrogen sulfate

HRID 530061Notes

Reaction equation

HRID 530061 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][N:2]1[C:7]1[N:12]=[C:11]([NH:13][CH2:14][CH2:15][CH3:16])[N:10]=[C:9]([NH:17][CH2:18][CH2:19][CH3:20])[N:8]=1.[OH:21][S:22]([OH:25])(=[O:24])=[O:23]>>[S:22]([OH:25])([OH:24])(=[O:23])=[O:21].[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][N:2]1[C:7]1[N:12]=[C:11]([NH:13][CH2:14][CH2:15][CH3:16])[N:10]=[C:9]([NH:17][CH2:18][CH2:19][CH3:20])[N:8]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 573779086-[1,2]oxazinan-2-yl-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 677731686-[1,2]Oxazinan-2-yl-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine hydrogen sulfate

Procedure

6-[1,2]Oxazinan-2-yl-N,N′-dipropyl-[1,3,5]triazine-2,4-diamine hydrogen sulfate (LVIII) was prepared from 6-[1,2]oxazinan-2-yl-N,N′-dipropyl-[1,3,5]triazine-2,4-diamine (LVII) and 95% H2SO4 as described in Example 20. Quantitative yield was isolated. 400 MHz 1H-NMR (DMSO-d6, ppm) 11.6-11.3 (1H, br s), 8.61-8.41 (0.8H, m), 8.18-8.03 (0.2H, m), 7.63-7.28 (1H, m), 4.14-4.08 (2H, m), 3.92-3.81 (2H, m, overlapped with water), 3.36-3.19 (4H, m), 1.86-1.78 (2H, m), 1.77-1.68 (2H, m), 1.6-1.45 (4H, m), 1.60-1.45 (6H, m). ESI-MS (m/z): 281 [M+H]+. M.P.: 134-137° C.

Workup

  1. customQuantitative yield was isolated

Sources & evidence

ORD record
ord-1d9af7d1a094438fa8b472c6a8487ad8
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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