Sulfuric Acid → HCID 86665991, compound

HRID 530080Notes

Reaction equation

HRID 530080 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]([NH:15][O:16][CH2:17][CH:18]([F:20])[F:19])[N:6]=1)[CH2:2][CH3:3].[OH:21][S:22]([OH:25])(=[O:24])=[O:23]>C(OCC)C.CCO>[S:22]([OH:25])([OH:24])(=[O:23])=[O:21].[CH2:1]([NH:4][C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH3:14])[N:8]=[C:7]([NH:15][O:16][CH2:17][CH:18]([F:20])[F:19])[N:6]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 57378018HCID 57378018, compound

Product 1

HCID 86665991HCID 86665991, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 3283Diethyl EtherSolvent

Procedure

N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-(2,2-difluoro-ethyl)-hydroxylamine (C, 1.02 g, 3.51 mmol) was reacted with 95% H2SO4 (0.19 mL, 3.51 mmol) in diethyl ether (3 mL) at 0° C. Two drops of EtOH were added, and the resultant crystals were filtered, washed with diethyl ether, and dried to yield N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-(2,2-difluoro-ethyl)-hydroxylamine hydrogen sulfate (CI) (1.26 g, 93%). 400 MHz 1H NMR (DMSO-d6, ppm) 11.8-10.5 (1H, m) 8.8-8.4 (0.3H, br s) 8.36-7.53 (1.7H, m) 6.50-6.08 (1H, m) 4.28-4.07 (2H, m) 3.39-3.13 (4H, m) 1.64-1.42 (4H, m) 0.97-0.78 (6H, m). ESI-MS (m/z) 291 [M±H]+. M.P.: 91-93° C.

Workup

  1. filtrationthe resultant crystals were filtered
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-68744cc92bb54292ba0285f42bd65880
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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