Triethylamine → 4-bromo-N,N-dimethylbenzamide

HRID 1177130

반응식

HRID 1177130 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]([CH3:14])[CH3:12])=[O:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 685154-Bromobenzoyl chloride

생성물 1

HCID 1403894-bromo-N,N-dimethylbenzamide수율 83.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-bromobenzoyl chloride (2.00 g, 9.11 mmol) and dimethyl amine hydrochloride (892 mg, 10.90 mmol) in 20 mL of CH2Cl2 was added triethylamine (3.81 mL, 27.30 mmol). The mixture was stirred at room temperature for 2 h, quenched with water, extracted with 3×CHCl3, dried with Na2SO4, concentrated and purified by Biotage column chromatography with 1-4% MeOH in 1:1 EtOAc/CH2Cl2 to give a white solid (1.73 g, 83% yield). 1H NMR (400 MHz, CDCl3) δ 7.48-7.65 (m, 2 H) 7.20-7.37 (m, 2 H) 3.05 (d, J=50.78 Hz, 6 H); LCMS for C9H10BrNO m/z 228.00 and 230.00 (M+H)+

후처리

  1. customquenched with water
  2. extractionextracted with 3×CHCl3
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by Biotage column chromatography with 1-4% MeOH in 1:1 EtOAc/CH2Cl2

출처 및 근거

ORD 기록
ord-dbe5a481fed240deb2d26db14fe096b8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

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