Water → 4-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide

HRID 241524

反応式

HRID 241524 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH3:11].CN(C)CCCN=C=NCC.[NH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26].O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:7])=[CH:4][C:3]=1[CH3:11]

参加物

7

反応物 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 821314-Bromo-3-methylbenzoic acidHCID 874881-(Trimethylsilyl)methylamine

生成物 1

HCID 668364694-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide収率 94%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 4-bromo-3-methylbenzoic acid (25 g) and 4-(dimethylamino)pyridine (“DMAP”, 2.1 g) in CH2Cl2 (320 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (“EDC”, 22.4 g) portionwise. Then, (aminomethyl)trimethylsilane (8.6 mL) was added, while cooling to keep the internal temperature below 20° C. The reaction was stirred at room temperature overnight. Water was added under vigorous stirring, and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phase dried (Na2SO4), and filtered over silica gel using CH2Cl2 and methyl tert-butyl ether (MTBE) to afford the title compound (32.8 g, 94%).

後処理

  1. temperaturewhile cooling
  2. customthe internal temperature below 20° C
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted twice with CH2Cl2
  5. dry with materialthe combined organic phase dried (Na2SO4)
  6. filtrationfiltered over silica gel

出典と根拠

ORDレコード
ord-84bff735b8e84773b38a246cec69f299
出典データセット
uspto-grants-2014_02
特許番号
US08653000B2

関連ノート

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