Sodium Azide → 4-(3-Azidoprop-2-ynyl)phenylacetic acid methyl ester

HRID 484454Notes

Reaction equation

HRID 484454 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[C:13]Cl)=[CH:7][CH:6]=1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[C:13][N:16]=[N+:17]=[N-:18])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 545437604-(3-Chloroprop-2-ynyl)phenylacetic acid methyl ester

Product 1

HCID 544964804-(3-Azidoprop-2-ynyl)phenylacetic acid methyl esterYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(3-Chloroprop-2-ynyl)phenylacetic acid methyl ester (5.3 g, 0.023M) was dissolved in dry dimethylformamide (30 ml) with sodium azide (1.7 g, 1.1 molar equivalents) and stirred at room temperature for 14 h. The reaction mixture was diluted with water (200 ml) and washed with dichloromethane (2×150 ml). The combined organic layers were washed with water (2×100 ml) and brine (1×100 ml) then dried (Na2SO4), filtered and concentrated in vacuo to give a residue which was purified by passage down a silica gel column, using as eluents 20% dichloromethane in hexane and finally neat dichloromethane, to give the required product (5.3 g) as a colourless oil. δ (360 MHz, CDCl3) 3.63 (2H, s, CH2CO2CH3), 3.70 (3H, s, CH2CO2CH3), 4.14 (2H, s, CH2N3), 7.24 (2H, d, J=8.4 Hz, ArH), 7.42 (2H, d, J=8.4 Hz, ArH); m/e 229 (M+).

Workup

  1. washwashed with dichloromethane (2×150 ml)
  2. washThe combined organic layers were washed with water (2×100 ml) and brine (1×100 ml)
  3. dry with materialthen dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by passage down a silica gel column

Sources & evidence

ORD record
ord-43ce6f4d1c424b51aba0b50fc82bf622
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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