Sodium Azide → HCID 21935318, compound

HRID 1241531Notes

Reaction equation

HRID 1241531 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[C:6]1[NH:7][C:8](=[O:27])[C:9]([I:26])=[C:10]([O:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]>CS(C)=O>[N:1]([C:6]1[NH:7][C:8](=[O:27])[C:9]([I:26])=[C:10]([O:17][C:18]2[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=2)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 21935319HCID 21935319, compound

Product 1

HCID 21935318HCID 21935318, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium azide (0.20 g, 3.12 mmol) was added to a solution of intermediate 3 (0.50 g, 1.56 mmol) in DMSO (5 ml), and the mixture was heated at 50° C. for 5 hours Reaction mixture was partitioned between water (30 ml) and ethyl acetate (40 ml). The organic layer was dried over magnesium sulfate and concentred. Flash chromatography (SiO2, CH2Cl2/ethanol 95:5) gave the desired product (0.49 g, 70%) as a white solid, m.p.=216–218° C.

Workup

  1. customReaction mixture
  2. customwas partitioned between water (30 ml) and ethyl acetate (40 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate

Sources & evidence

ORD record
ord-414d32aa17084f4fa490c058e0e0f424
Source dataset
uspto-grants-2006_10
Patent number
US07115608B2

Reaction notes

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