4,6-Dichloro-1,3,5-trazin-2-amine → Methyl 3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]benzoate

HRID 341489Notes

Reaction equation

HRID 341489 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[OH-].[Na+].[Cl:14][C:15]1[N:20]=[C:19](Cl)[N:18]=[C:17]([NH2:22])[N:16]=1>CC#N.O>[NH2:22][C:17]1[N:16]=[C:15]([Cl:14])[N:20]=[C:19]([NH:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[N:18]=1

Participants

5

Reactant 3

HCID 136154,6-Dichloro-1,3,5-trazin-2-amineHCID 14798Sodium HydroxideHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 86710519Methyl 3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]benzoateYield 87%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Methyl 3-aminobenzoate (0.69 g, 4.55 mmol) and a 1N NaOH aqueous solution (0.91 mL, 0.91 mmol) were added to a solution of 4,6-dichloro-1,3,5-triazin-2-amine (0.75 g, 4.55 mmol) in a 1:1 MeCN/water mixture (40 mL) at 0 C. The mixture was stirred at 0 C for 1 h and room temperature for 3 days. The acetonitrile was removed under vacuum and the resulting white solid in water was filtered and dried under vacuum to provide the title compound (1.1 g, 87%). Method B HPLC-MS: MH+ requires m/z=280/282 Found: m/z=280/282, Rt=1.69 min (95%).

Workup

  1. customThe acetonitrile was removed under vacuum
  2. filtrationthe resulting white solid in water was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a63e938dbe5747b8b17ce59b15f40ac8
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

Loading…