Propylamine → HCID 86015661, compound

HRID 1752109Notes

Reaction equation

HRID 1752109 reaction equation
[OH-].[Na+].Cl[C:4]1[N:9]=[C:8](Cl)[N:7]=[C:6](Cl)[N:5]=1.[CH2:12]([NH2:15])[CH2:13][CH3:14]>CC(C)=O.O>[CH2:12]([NH:15][C:4]1[N:9]=[C:8]([NH:15][CH2:12][CH2:13][CH3:14])[N:7]=[CH:6][N:5]=1)[CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 7852PropylamineHCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 86015661HCID 86015661, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 2 M NaOH solution (163 mL, 325.36 mmol) was added in a dropwise manner to a suspension of 2,4,6-trichloro-1,3,5-triazine (XVIII) (30.0 g, 162.68 mmol) and n-propylamine (26.8 mL, 325.36 mmol) in acetone (600 mL) and water (30 mL) at 0° C. (water—ice/NaCl bath). The ice bath was removed and the reaction mixture was heated at 50° C. for 3 h, then cooled. Water (200 mL) was added to the reaction mixture; the precipitate was filtered, washed with water (200 mL) and dried over P2O5 at 40° C. for 20 h to yield 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV, 33.6 g, 90% yield). 400 MHz 1H NMR (DMSO-d6, ppm) 7.80 (0.85H, t, J=5.5 Hz), 7.76-7.66 (1H, m), 7.49 (0.15H, t, J=5.5 Hz), 3.22-3.11 (4H, m), 1.55-1.42 (4H, m), 0.88-0.82 (6H, m). ESI-MS (m/z): 230, 232 [M+H]+.

Workup

  1. customThe ice bath was removed
  2. temperaturecooled
  3. additionWater (200 mL) was added to the reaction mixture
  4. filtrationthe precipitate was filtered
  5. washwashed with water (200 mL)
  6. dry with materialdried over P2O5 at 40° C. for 20 h

Sources & evidence

ORD record
ord-3cd0adfd425f42d0ad1220662d676e0b
Source dataset
uspto-grants-2015_10
Patent number
US09162992B2

Reaction notes

Loading…