Sodium Azide → HCID 19696171, compound

HRID 863485Notes

Reaction equation

HRID 863485 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH2:13][CH:12](OS(C)(=O)=O)[CH2:11][CH2:10]2)(=[O:3])[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH:12]1[CH2:13][C:14]2[C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:10][CH2:11]1)=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86752143HCID 86752143, compound

Product 1

HCID 19696171HCID 19696171, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methanesulfonic acid 8-acetylamino-1,2,3,4-tetrahydronaphthalen-2-yl ester (3.8 g, 13 mmol) and sodium azide (1.7 g, 27 mmol) in dimethylformamide (70 mL) was heated at 50° C. for 6 h. The solvent was removed by rotoevaporation in vacuo and the residue partitioned between methylene chloride and water. The organic layer was separated, dried over sodium sulfate, filtered and evaporated to give a dark solid. The product was purified by column chromatography on silica gel (1:1 ethyl acetate:hexane as eluant) to give a white solid (2.9 g) in 97% yield.

Workup

  1. customThe solvent was removed by rotoevaporation in vacuo
  2. customthe residue partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a dark solid
  8. customThe product was purified by column chromatography on silica gel (1:1 ethyl acetate:hexane as eluant)

Sources & evidence

ORD record
ord-4b8e14f1353a4317a91ae19bbe85c6bf
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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