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4-Bromo-2-methoxy-6-methylaniline → N-(4-Bromo-2-methoxy-6-methylphenyl)-4-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-2-amine

HRID 1698558
ノート
印刷プレビュー

反応式

HRID 1698558 の反応式
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=[C:11]([Cl:12])[C:4]=2[N:3]=1.[Br:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:22]([NH2:23])=[C:21]([O:27][CH3:28])[CH:20]=1>CN1CCCC1=O.C(OCC)(=O)C.O>[Br:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:22]([NH:23][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:10]=[C:11]([Cl:12])[C:4]=3[N:3]=2)=[C:21]([O:27][CH3:28])[CH:20]=1
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 106802184-Bromo-2-methoxy-6-methylanilineHCID 672730252,4-Dichloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole

生成物 1

HCID 11977538N-(4-Bromo-2-methoxy-6-methylphenyl)-4-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-2-amine収率 49.1%

試薬・触媒・溶媒 2

HCID 13387N-methyl-2-pyrrolidone触媒HCID 22728543Water ethylacetate
溶媒

反応条件

温度
130 °C

実験手順

A mixture of 2,4-dichloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole (140 mg, 0.52 mmol), 4-bromo-2-methoxy-6-methylaniline (335 mg, 1.55 mmol) and 1-methyl-2-pyrrolidone (5 drops) was stirred at 130° C. for 2 days under nitrogen atmosphere. The mixture was dissolved in ethyl acetate/water, extracted with ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, and concentrated to give a brown oil. The oil was subjected to chromatography on a silica gel (n-hexane/ethyl acetate=10:1-1:1) and crystallized from iso-propanol to afford the title compound as colorless crystals (115 mg, 49%). mp. 218-220° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a brown oil
  6. customcrystallized from iso-propanol

出典と根拠

ORDレコード
ord-3a233be1286149ef8ebda5b23d3989da
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

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