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Sodium hydride → 6,7-dichloro-2,3-dimethoxy-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-ylmethyl]quinoxaline

HRID 1957132
ノート
印刷プレビュー

反応式

HRID 1957132 の反応式
Cl.[CH3:2][N:3]([CH2:5][C:6]1[CH:14]=[CH:13][C:9]2[NH:10][N:11]=[N:12][C:8]=2[CH:7]=1)[CH3:4].[H-].[Na+].Br[CH2:18][C:19]1[C:28]([Cl:29])=[C:27]([Cl:30])[CH:26]=[C:25]2[C:20]=1[N:21]=[C:22]([O:33][CH3:34])[C:23]([O:31][CH3:32])=[N:24]2.[Cl-].[NH4+]>CN(C)C=O.O>[Cl:29][C:28]1[C:19]([CH2:18][N:10]2[C:9]3[CH:13]=[CH:14][C:6]([CH2:5][N:3]([CH3:2])[CH3:4])=[CH:7][C:8]=3[N:12]=[N:11]2)=[C:20]2[C:25](=[CH:26][C:27]=1[Cl:30])[N:24]=[C:23]([O:31][CH3:32])[C:22]([O:33][CH3:34])=[N:21]2
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

7

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 105459165-Bromomethyl-6,7-dichloro-2,3-dimethoxyquinoxalineHCID 178483163HCID 178483163、化合物

生成物 1

HCID 543919756,7-dichloro-2,3-dimethoxy-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-ylmethyl]quinoxaline収率 28%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
-30 °C

実験手順

5-(N,N-Dimethylaminomethyl)-1H-1,2,3-benzotriazole hydrochloride (383 mg 1.8 mmol) was added to a suspension of sodium hydride (108 mg, 80% dispersion in oil, 3.6 mmol) in dry dimethylformamide (20 mL) at room temperature and stirred for 15 minutes. The mixure was cooled to -30° C., 5-bromomethyl-6,7-dichloro-2,3-dimethoxy quinoxaline (Preparation 1, 528 mg, 1.5 mmol) was added, and the mixture was stirred at -30° C. for 1 hour, and then allowed to warm slowly to 0° C. Saturated aqueous ammonium chloride (5 mL) was added, followed by water (50 mL). The product was extracted into ethyl acetate, the extracts were washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane/ethyl acetate, then ethyl acetate/methanol) to give 6,7-dichloro-2,3-dimethoxy-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-yl] methylquinoxaline (135 mg, 28%), Rf =0.4 (silica gel, ethyl acetate/methanol=4:1), as the slowest eluted product isomer.

後処理

  1. stirringthe mixture was stirred at -30° C. for 1 hour
  2. temperatureto warm slowly to 0° C
  3. extractionThe product was extracted into ethyl acetate
  4. washthe extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (
  8. washgradient elution with hexane/ethyl acetate

出典と根拠

ORDレコード
ord-895bcb967bc244aa8904eb75c5378bc3
出典データセット
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05783572

反応ノート

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