Sodium Azide → 4-(Azidomethyl)-2,6-dihydroxymethyl-s-triazine
Reaction equation
C1(C)C=CC(S([CH2:10][C:11]2[N:16]=[C:15]([CH2:17][OH:18])[N:14]=[C:13]([CH2:19][OH:20])[N:12]=2)(=O)=O)=CC=1.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:10][C:11]1[N:12]=[C:13]([CH2:19][OH:20])[N:14]=[C:15]([CH2:17][OH:18])[N:16]=1)=[N+:23]=[N-:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
4-(p-Toluenesulfonylmethyl)-2,6-dihydroxymethyl-s-triazine is dissolved in DMF and sodium azide (1.1 eq.) is added. The reaction mixture is heated to 50° C. for 4 hours. The DMF is removed under reduced pressure and the residue is partitioned between CH2Cl2 and water. The CH2Cl2 layer is separated and the water layer is extracted several times with CH2Cl2. The CH2Cl2 layers are combined, dried (MgSO4), and concentrated. The resultant residue is purified by silica gel flash column chromatography to give 4-(azidomethyl)-2,6-dihydroxymethyl-s-triazine.