Ethyl propiolate → HCID 90460390, compound

HRID 2202105Notes

Reaction equation

HRID 2202105 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[C:13]#[CH:14]>C(O)C>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([N:1]2[C:13]([C:12]([O:16][CH2:17][CH3:18])=[O:15])=[CH:14][N:3]=[N:2]2)=[CH:11][CH:10]=1)#[N:9]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 5756914-azidobenzonitrile

Product 1

HCID 90460390HCID 90460390, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-azidobenzonitrile (5.3 g, 36.77 mmol, 1.00 equiv) and ethyl prop-2-ynoate (10.82 g, 110.30 mmol, 3.00 equiv) in ethanol (160 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to give 650 mg (7%) of ethyl 1-(4-cyanophenyl)-1H-1,2,3-triazole-5-carboxylate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.54 (s, 1H), 8.11 (d, J=8.0 Hz, 2H), 7.90 (d, J=8.0 Hz, 2H), 4.27-4.22 (m, 2H), 1.20 (t, J=6.8 Hz, 3H) ppm. LCMS (method C, ESI): RT=0.87 min, m/z=243.1 [M+H]+ and 2.4 g (26%) of ethyl 1-(4-cyanophenyl)-1H-1,2,3-triazole-4-carboxylate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.66 (s, 1H), 8.24 (d, J=8.8 Hz, 2H), 8.13 (d, J=8.8 Hz, 2H), 4.41-4.36 (m, 2H), 1.36 (t, J=7.2 Hz, 3H) ppm. LCMS (method D, ESI): RT=1.71 min, m/z=243.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified on a silica gel column
  3. washeluted with 0-20% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-12e5c29a728e4eceb9b3740cecbd86c5
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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