1-(2-Bromoethyl)naphthalene → 4,6-Diamino-1,2-dihydro-2,2-dimethyl-1-[2-(naphth-1-yl)ethoxy]-1,3,5-triazine hydrobromide

HRID 1463287Notes

Reaction equation

HRID 1463287 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]([OH:9])[C:4]([CH3:11])([CH3:10])[N:3]=1.[C:12]1([CH2:22][CH2:23][Br:24])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[BrH:24].[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]([O:9][CH2:23][CH2:22][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[C:4]([CH3:11])([CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 1395411-(2-Bromoethyl)naphthaleneHCID 190899224,6-Diamino-1,2-dihydro-1-hydroxy-2,2-dimethyl-1,3,5-triazine

Product 1

HCID 190899464,6-Diamino-1,2-dihydro-2,2-dimethyl-1-[2-(naphth-1-yl)ethoxy]-1,3,5-triazine hydrobromideYield 20.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to that of Example 3, Step F, using 0.8 gram (0.005 mole) of 4,6-diamino-1,2-dihydro-1-hydroxy-2,2-dimethyl-1,3,5-triazine (prepared in Example 3) and 1.3 grams (0.006 mole) of 2-(naphth-1-yl)ethyl bromide (commercially available) in 15 ml of dimethylformamide. The reaction product was recrystallized from water, yielding 0.4 gram of 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-[2-(naphth-1-yl)ethoxy]-1,3,5-triazine hydrobromide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 3, Step F
  2. customThe reaction product was recrystallized from water

Sources & evidence

ORD record
ord-f6b1f6c2e4574b6999a1c1ca9d3208b9
Source dataset
uspto-grants-1994_04
Patent number
US05300503

Reaction notes

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