Sodium Azide → HCID 451826, compound

HRID 1904997Notes

Reaction equation

HRID 1904997 reaction equation
[CH2:1]([C:3]1[C:4](=[O:28])[NH:5][C:6](=[O:27])[N:7]([CH:26]=1)[C@@H:8]1[O:25][C@H:12]([CH2:13]OS(C2C=CC(C)=CC=2)(=O)=O)[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[N-:29]=[N+:30]=[N-:31].[Na+].[N-]=[N+]=[N-].[Li+]>CN(C)C=O>[N:29]([CH2:13][C@H:12]1[O:25][C@@H:8]([N:7]2[CH:26]=[C:3]([CH2:1][CH3:2])[C:4](=[O:28])[NH:5][C:6]2=[O:27])[CH2:9][C@@H:10]1[OH:11])=[N+:30]=[N-:31]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 88163Lithium azideHCID 5280128HCID 5280128, compound

Product 1

HCID 451826HCID 451826, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-ethyl-5'-O-tosyl-2'-deoxyuridine (550 mg, 1.34 mmole) and sodium azide (480 mg, 7.4 mmole) or lithium azide (400 mg) in dry dimethylformamide (10 ml) is heated at 85° C. for 2 hr. Tlc indicates all the starting material has reacted. The solvent is evaporated in vacuo to dryness, and the remaining material is triturated with ice-cold water, filtered to collect the product, and dried over P2O5 to give a white solid (340 mg, 90%), m.p. 174°-177° C.

Workup

  1. customhas reacted
  2. customThe solvent is evaporated in vacuo to dryness
  3. customthe remaining material is triturated with ice-cold water
  4. filtrationfiltered
  5. customto collect the product
  6. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-d24fc668edc6440e92e842b1ea1d5b27
Source dataset
uspto-grants-1989_06
Patent number
US04841039

Reaction notes

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