4-Benzyloxybenzoylchloride → HCID 44128288, compound
Reaction equation
[OH:1]/[N:2]=[C:3](\[NH2:17])/[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1.[CH2:18]([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[CH:6][C:7]([O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[CH:8][CH:9]=3)[N:17]=2)=[CH:33][CH:34]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(Z)-N′-Hydroxy-4-(pyridin-2-yloxy)benzamidine (339 mg, 137 μmol) and 4-benzyloxybenzoyl chloride (24 mg, 106 μmol) were suspended in pyridine (2.0 mL) the solution was refluxed for 21 hours. The reaction mixture was then cooled to room temperature and solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (Hex/EtOAc 2:1) to give the product as a white solid (20 mg, 46%). 1H NMR (500 MHz, CDCL3) δ(ppm): 5.16 (2H, s), 6.99 (1H, d, J=8.2 Hz), 7.05 (1H, ddd, J=7.2, 5.0, 0.80 Hz), 7.11 (2H, d, J=8.8 Hz), 7.27 (2H, d, J=8.8 Hz), 7.34-7.38 (1H, m), 7.40-7.46 (4H, m), 7.73 (1H, ddd, J=8.8, 8.2, 2.0 Hz), 8.16 (2H, d, J=9.0 Hz), 8.20 (2H, d, J=8.6 Hz), 8.24 (1H, dd, J=5.0, 2.0Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 70.4 (CH2), 112.3 (CH), 115.5 (CH), 117.3, 119.3 (CH), 121.4 (CH), 123.5, 127.7 (CH), 128.5 (CH), 128.9 (CH), 129.3 (CH), 130.3 (CH), 136.2, 139.9 (CH), 148.0 (CH), 156.8, 162.5, 163.3, 168.5, 175.7. MS (FAB+): 422 (MH+). HRMS for C26H19N3O3 (MH+): calculated: 422.1505; found 422.1505.