Sodium Hydroxide → 4-Amino-6-[(2,2-dimethoxyethyl)amino]-1,3,5-triazin-2(5H)-one

HRID 1389911Notes

Reaction equation

HRID 1389911 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([OH:9])[N:3]=1.[OH-].[Na+].[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][NH2:16]>O>[NH2:1][C:2]1[NH:3][C:4](=[O:9])[N:5]=[C:6]([NH:16][CH2:15][CH:14]([O:17][CH3:18])[O:13][CH3:12])[N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 178509008HCID 178509008, compound

Product 1

HCID 1358398444-Amino-6-[(2,2-dimethoxyethyl)amino]-1,3,5-triazin-2(5H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2-amino-4-chloro-6-hydroxy-s-triazine (II) 15.0 g, 0.102 mol) in 250 mL of water was treated with sodium hydroxide (4.095 g, 0.102 mol), and the mixture was stirred to obtain a clear solution which was treated with aminoacetaldehyde dimethyl acetal (12.9 g, 0.12 mol). The mixture was heated under gentle reflux for 2.5 h. with stirring and then cooled to room temperature. The crystalline solid that separated was collected and washed with cold water (2×25 mL). Recrystallization from a large excess of water gave the compound as needles: 15.0 g (68.0%); mp 285° C. dec. Anal. (C7H13N5O3, 215.21) C, H, N.

Workup

  1. customto obtain a clear solution which
  2. temperatureThe mixture was heated
  3. temperatureunder gentle reflux for 2.5 h.
  4. stirringwith stirring
  5. customThe crystalline solid that separated
  6. customwas collected
  7. washwashed with cold water (2×25 mL)
  8. customRecrystallization from a large excess of water

Sources & evidence

ORD record
ord-aad68c6b805847b7899816ff0e67cf72
Source dataset
uspto-grants-1981_01
Patent number
US04246408

Reaction notes

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