Pyridine → HCID 57907147, compound

HRID 2113910Notes

Reaction equation

HRID 2113910 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[CH:12])[CH:6]=1)[CH3:2].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[N:22][OH:23])=[CH:17][CH:16]=1.N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[O:23][N:22]=[C:21]([C:18]3[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=3)[CH:12]=2)[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27555434-chloro-N-hydroxybenzene-1-carbonimidoyl chlorideHCID 15540684Ethyl 3-ethynylbenzoate

Product 1

HCID 57907147HCID 57907147, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a 10 ml round flask, 500 mg (2.9 mmol) of 3-ethynyl-benzoic acid ethyl ester and 652 mg (3.5 mmol, 1.2 eq.) of 4-chloro-N-hydroxy-benzenecarboximidoyl chloride are dissolved in 4 ml of CHCl3. To this solution, 11 mg (0.14 mmol, 0.05 eq.) of pyridine and 290 mg (2.9 mmol) of triethyl amine are added at 0° C. under a nitrogen atmosphere. The orange solution is stirred under warming to room temperature for 20 h. The suspension is filtered and the solution concentrated in vacuo. Chromatographical purification (100 g SiO2; eluent: hexane/ethyl acetate 9:1) yields the title compound as a white solid. Mass spectrum: m/z (M+H)+: 328.2; 330.2

Workup

  1. filtrationThe suspension is filtered
  2. concentrationthe solution concentrated in vacuo
  3. customChromatographical purification (100 g SiO2; eluent: hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-daba3c1af9284ba79c5d5e41ec0201fe
Source dataset
uspto-grants-2008_10
Patent number
US07432293B2

Reaction notes

Loading…