Triethylamine → 4-bromo-N,N-dimethylbenzamide

HRID 1177130ノート

反応式

HRID 1177130 の反応式
[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

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 685154-Bromobenzoyl chloride

生成物 1

HCID 1403894-bromo-N,N-dimethylbenzamide収率 83.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-dbe5a481fed240deb2d26db14fe096b8
出典データセット
uspto-grants-2010_11
特許番号
US07842713B2

反応ノート

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