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Tetramethyltin → 7-(1-Ethylpropyl)-1,4-dimethyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 1698563
ノート
印刷プレビュー

反応式

HRID 1698563 の反応式
Br[C:2]1[C:10]2[NH:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[C:5]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:4][CH:3]=1.[CH3:18][Sn](C)(C)C>CN(C)P(=O)(N(C)C)N(C)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:14]([CH:13]([C:5]1[C:6]2[N:7]([CH3:12])[C:8](=[O:11])[NH:9][C:10]=2[C:2]([CH3:18])=[CH:3][CH:4]=1)[CH2:16][CH3:17])[CH3:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 11661TetramethyltinHCID 672727554-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

生成物 1

HCID 672728947-(1-Ethylpropyl)-1,4-dimethyl-1,3-dihydro-2H-benzimidazol-2-one収率 57.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒
HCID 12679
Hexamethylphosphoramide
溶媒

実験手順

A solution of 4-bromo-7-(1-ethylpropyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (250 mg, 0.84 mmol), tetrakis(triphenylphosphine)palladium (194 mg, 0.168 mmol), tetramethyltin (1.16 mL, 8.4 mmol) in hexamethylphosphoric triamide (5 mL) was refluxed for 18 h. After cooling, the mixture was diluted with water and extracted with dichloromethane. The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on a silica gel (n-hexane/ethyl acetate=90:10-50:50) to give the title compound (111 mg, 0.48 mmol, 57%).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on a silica gel (n-hexane/ethyl acetate=90:10-50:50)

出典と根拠

ORDレコード
ord-f2d66bba8b4b49af8722f6f883f468b5
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163935B2

反応ノート

読み込み中…

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