4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane → 4-(Azidomethyl)-2,2-dimethyl-1,3-dioxolane

HRID 903196Notes

Reaction equation

HRID 903196 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7]Cl)[CH2:4][O:3]1.[N-:10]=[N+:11]=[N-:12].[Na+]>CN(C=O)C>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][N:10]=[N+:11]=[N-:12])[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 33557Sodium Azide

Product 1

HCID 115356024-(Azidomethyl)-2,2-dimethyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.05 g. of 2,2-dimethyl-4-chloromethyl-1,3-dioxolane is dissolved in 100 ml. DMF and 6.5 g. of NaN3 are added. The mixture is stirred at 50° overnight, cooled to room temperature, diluted with 300 ml. C6H6 and washed 5 times with water. The organic phase is dried and evaporated under reduced pressure to give 2,2-dimethyl-4-azidomethyl-1,3-dioxolane.

Workup

  1. additiondiluted with 300 ml
  2. washC6H6 and washed 5 times with water
  3. customThe organic phase is dried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cec873b6dcb746b281cfd8740518e9f1
Source dataset
uspto-grants-1980_10
Patent number
US04226866

Reaction notes

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