1,2-Dichloroethane → 2-Bromo-N-methoxy-N,5-dimethylbenzamide

HRID 501712

반응식

HRID 501712 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2280802-Bromo-5-methylbenzoic acid

생성물 1

HCID 534166972-Bromo-N-methoxy-N,5-dimethylbenzamide수율 55%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Step AI (1): To a solution of 2-bromo-5-methylbenzoic acid (1000.0 mg, 4.65 mmol) in DMF (100 mL) were added N,O-dimethylhydroxylamine hydrochloride (454 mg, 4.65 mmol), EDC (891 mg, 4.65 mmol), and HOBT (628 mg, 4.65 mmol). The reaction mixture was stirred at rt for 2.5 days. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography to give 2-bromo-N-methoxy-N,5-dimethylbenzamide (656 mg, 55%) as a colorless oil. LC-MS (M+H)+=258.21.

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-8650cec7e005429a8345bcad56f16495
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772221B2

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