Hydrochloric Acid → HCID 178456887, compound

HRID 1752158Notes

Reaction equation

HRID 1752158 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.[OH-:16].[Na+].O.Cl>O1CCOCC1>[CH2:13]([NH:12][C:4]1[N:5]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:7]=[C:2]([OH:16])[N:3]=1)[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 183046-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamine

Product 1

HCID 178456887HCID 178456887, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A vial was charged with 6-chloro-N2,N4-dipropyl-1,3,5-triazine-2,4-diamine (XXXIV) (800 mg, 3.48 mmol), NaOH (696 mg, 17.40 mmol), water (3 mL) and 1,4-dioxane (3 mL). The reaction mixture was heated at 140° C. for 30 min under microwave irradiation. The mixture was acidified with 1N HCl to pH 5, precipitate were filtered, washed with water. The product was dissolved in 50% trifluoroacetic acid (30 mL), the indissoluble residue was filtered off. The filtrate was neutralized with saturated NaHCO3 solution, the formed precipitate was filtered, washed with water, acetone and dried to give 550 mg (75%) of 4,6-bis(propylamino)-1,3,5-triazin-2-ol (CLXXVIII). 400 MHz 1H NMR (DMSO-d6+CF3COOD, ppm) 3.18-3.34 (4H, m), 1.45-1.59 (4H, m), 0.86 (6H, t). ESI-MS (m/z): 212 [M+H]+.

Workup

  1. filtrationwere filtered
  2. washwashed with water
  3. dissolutionThe product was dissolved in 50% trifluoroacetic acid (30 mL)
  4. filtrationthe indissoluble residue was filtered off
  5. filtrationthe formed precipitate was filtered
  6. washwashed with water, acetone
  7. customdried

Sources & evidence

ORD record
ord-3bf9b0cf9f1c40d2bfafcb1fe6e9a136
Source dataset
uspto-grants-2015_10
Patent number
US09162992B2

Reaction notes

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