Pyridine → 5-chloro-N,N-diethyl-2-iodobenzamide

反応式

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[N:12]1[CH:17]=[CH:16]C=[CH:14][CH:13]=1.O1CCCC1.C(NCC)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7]([N:12]([CH2:17][CH3:16])[CH2:13][CH3:14])=[O:8]

参加物

反応物 4

HCID 1049Pyridine

HCID 8021Diethylamine

HCID 8028Tetrahydrofuran

HCID 866015855-Chloro-2-iodobenzoyl chloride

生成物 1

HCID 681829545-chloro-N,N-diethyl-2-iodobenzamide収率 61%

実験手順

In a 100 mL round bottomed flask was placed the 5-chloro-2-iodobenzoyl chloride prepared above. Pyridine (50 mL, 600 mmol) and tetrahydrofuran (10 mL, 100 mmol) were then added. To the reaction mixture was added diethylamine (3 mL, 30 mmol) and the mixture was stirred for 3 hr at rt. The mixture was stirred for an additional 3 hr at 50° C. The mixture was allowed to cool to rt and then concentrated under reduced pressure. The residue was dissolved in EtOAc (100 mL) and then washed with 1N HCl (50 mL×2), 1N NaOH (50 mL), brine (50 mL), and dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain the title compound (1.96 g, 61%) as a light yellow syrup. LCMS: (FA) ES+ 338, 340; 1H NMR (300 MHz, d6-DMSO) δ ppm 7.86 (d, 1H), 7.38 (d, 1H), 7.21 (dd, 1H), 3.61-3.68 (m, 1H), 2.91-3.29 (m, 3H), 1.17 (t, 3H), 1.01 (t, 3H).