Methylamine → HCID 16082, compound

HRID 1678438Notes

Reaction equation

HRID 1678438 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[NH2:15][CH3:16].[OH-].[Na+]>CC#N.O>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=[C:2]([NH:15][CH3:16])[N:7]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 155492,4-Dichloro-6-phenyl-1,3,5-triazine

Product 1

HCID 16082HCID 16082, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-dichloro-6-phenyl-1,3,5-triazine (16.0 g, 70.8 mmol, 1.00 equiv) dissolved in 1:1 CH3CN:H2O (80 mL) was cooled (0° C.), and a solution of NH2Me (8.00 g, 27.5% solution in H2O, 70.8 mmol, 1.00 equiv) was added. The pH of the reaction mixture was adjusted to 9-10 by treating with 1 N NaOH. The pH was maintained at 9-10 for 15 min (product formation monitored by LCMS). The mixture was diluted with water, and filtered to provide 12 g of crude product (filtered solid was washed with additional water). A portion of this material (8 g) was purified by HPLC to afford 3.6 g of the title compound. MS (ES+): m/e 221.1 [M+H]+.

Workup

  1. temperatureThe pH was maintained at 9-10 for 15 min (product formation monitored by LCMS)
  2. filtrationfiltered
  3. customto provide 12 g of crude product (filtered solid was washed with additional water)
  4. customA portion of this material (8 g) was purified by HPLC

Sources & evidence

ORD record
ord-e9d8394f9e3d4553be4a8b78a6c9dc0a
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

Loading…