Sodium Azide → 4-(Azidomethyl)-2,6-dihydroxymethyl-s-triazine

HRID 1531457Notes

Reaction equation

HRID 1531457 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

HCID 33557Sodium AzideHCID 223236944-(p-Toluenesulfonylmethyl)-2,6-dihydroxymethyl-s-triazine

Product 1

HCID 223236434-(Azidomethyl)-2,6-dihydroxymethyl-s-triazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. customThe DMF is removed under reduced pressure
  2. customthe residue is partitioned between CH2Cl2 and water
  3. customThe CH2Cl2 layer is separated
  4. extractionthe water layer is extracted several times with CH2Cl2
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe resultant residue is purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-ac0f6e1f8af84e81a3d917a516c35e62
Source dataset
uspto-grants-2001_03
Patent number
US06197965B1

Reaction notes

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