Oxalyl chloride → 4-Chloro-3-(3,5-dichloro-pyridin-2-yl)benzoyl chloride

HRID 661647노트

반응식

HRID 661647 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1.C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:22])=[O:7])=[CH:4][C:3]=1[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1

참가 물질

5

반응물 2

HCID 65578Oxalyl chlorideHCID 686040024-Chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid

생성물 1

HCID 866425734-Chloro-3-(3,5-dichloro-pyridin-2-yl)benzoyl chloride

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

To 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid (100 mg, 0.33 mmol) in dry DCM (1 mL), was added DMF (1 drop) followed by addition of oxalyl chloride (35 μL, 0.40 mmol) slowly. The mixture was stirred for 2.5 hrs, then concentrated to yield 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoyl chloride, which was dissolved in DCM (1 mL). 2-Methylamino-phenol (45 mg, 0.36 mmol) was added followed by the slow addition of diisopropylethylamine (88 μL, 0.5 mmol). The mixture was stirred at room temperature for 12 hrs, concentrated and purified by preparative TLC (DCM/MeOH=9/1) followed by preparative LCMS to yield 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide 19-1. MS (M+H)+: 409.0, tR=7.55 min (method 2)

후처리

  1. concentrationconcentrated

출처 및 근거

ORD 기록
ord-471ac3a636c741d4af55acbbbe96e40d
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084614B2

반응 노트

불러오는 중…