Cyanuric chloride → N-(3-azidopropyl)-4,6-dichloro-1,3,5-triazin-2-amine

HRID 1404415Notes

Reaction equation

HRID 1404415 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.C(N(C(C)C)CC)(C)C.[N:19]([CH2:22][CH2:23][CH2:24][NH2:25])=[N+:20]=[N-:21]>CC(C)=O>[N:19]([CH2:22][CH2:23][CH2:24][NH:25][C:2]1[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([Cl:6])[N:4]=1)=[N+:20]=[N-:21]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 81531DiisopropylethylamineHCID 1501103-Azidopropan-1-amine

Product 1

HCID 86672179N-(3-azidopropyl)-4,6-dichloro-1,3,5-triazin-2-amineYield 45.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of cyanuric chloride (18.42 g, 0.10 mol) in acetone (180 mL) in an ice-water bath was added diisopropylethylamine (DIPEA) (12.92 g, 0.10 mol). 1-azido-3-aminopropane (5.00 g, 0.050 mol) in acetone (50 mL) was added slowly over 2 hours. The reaction was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, washed with water, dried (Na2SO4) and rotary evaporated. The resulting residue was purified by column chromatography on silica gel (eluent CH2Cl2) to give 1 as a white solid (5.62 g, 45%): ESI-MS m/z 248.1 (M+H+) calculated for C6H8Cl2N7 248.0.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialdried (Na2SO4) and rotary evaporated
  5. customThe resulting residue was purified by column chromatography on silica gel (eluent CH2Cl2)

Sources & evidence

ORD record
ord-9b9522b2d31340ccb5a87aa75cc45e6f
Source dataset
uspto-grants-2014_12
Patent number
US08912323B2

Reaction notes

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