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Dimethylamine tetrahydrofuran → 4-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide

HRID 2239297
ノート
印刷プレビュー

反応式

HRID 2239297 の反応式
Br[C:2]1[CH:3]=[C:4]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[CH:21]=1.[O:30]1[CH2:34]CCC1.[CH3:35][NH:36][CH3:37]>C(OCC)(=O)C.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>[CH3:35][N:36]([CH3:37])[C:34]([C:2]1[CH:3]=[C:4]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([S:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)(=[O:13])=[O:12])[C:6]=2[CH:21]=1)=[O:30]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 22320367Dimethylamine tetrahydrofuranHCID 67219535HCID 67219535、化合物

生成物 1

HCID 672201744-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide収率 42%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

A mixture of 6-bromo-2-methyl-1-[(4-methylphenyl)sulfonyl]-4-[(phenylmethyl)oxy]-1H-benzimidazole (53.0 g, 112 mmol, STEP 2) and tetrakis(triphenylphosphine)palladium(0) (25.9 g, 22.4 mmol) in 2M dimethylamine tetrahydrofuran solution (580 mL) was stirred at 65° C. under carbon mono-oxide gas (1 atmosphere) for 32 hours. The mixture was cooled to room temperature, and diluted with ethyl acetate (600 mL). The organic mixture was washed with saturated ammonium chloride aqueous solution (800 mL) and brine (500 mL), dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate gradient elution from 1:2 to 1:3) to afford the title compound as a white solid (21.8 g, 42%).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic mixture was washed with saturated ammonium chloride aqueous solution (800 mL) and brine (500 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate gradient elution from 1:2 to 1:3)

出典と根拠

ORDレコード
ord-6d5cb90a823b4ba69bc72c8abc6d4df6
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07723321B2

反応ノート

読み込み中…

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