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Hydrochloric Acid → 2-{4-[2-(2-Nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazole

HRID 339489
ノート
印刷プレビュー

反応式

HRID 339489 の反応式
[O:1]([C:3]1[CH:26]=[CH:25][C:6]2[N:7]=[C:8]([C:10]3[CH:24]=[CH:23][C:13]([CH2:14]P(=O)(OCC)OCC)=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1)[CH3:2].[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O)([O-:29])=[O:28].C[O-].[Na+].Cl>CO.O>[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=[CH:14][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[S:9][C:5]3[CH:4]=[C:3]([O:1][CH3:2])[CH:26]=[CH:25][C:6]=3[N:7]=2)=[CH:24][CH:23]=1)([O-:29])=[O:28]
参加物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 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 10942334Sodium MethoxideHCID 13599215Diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate

生成物 1

HCID 672367122-{4-[2-(2-Nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazole収率 44.3%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 962Water溶媒

実験手順

To a stirred solution of diethyl 4-(6-methoxylbenzothiazol-2-yl)benzylphosphonate (0.10 g, 0.25 mmol) and 2-nitrobenzaldehyde (0.39 g, 0.25 mmol) in dry MeOH (10 ml) at 0° C. was added dropwise a solution of 0.5 M sodium methoxide (1.02 ml, 0.51 mmol). The reaction mixture was then allowed to rise to room temperature and heated under reflux for 18 h. The reaction mixture was cooled to room temperature and water (30 ml) was added followed by 1 M HCl until the reaction mixture became acidic. The reaction mixture was then extracted with DCM (3×80 ml) and the combined organic extracts washed with brine (50 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a solid which was purified by flash chromatography (DCM) to give the title compound (0.043 g, 43%) as a yellow solid.

後処理

  1. customto rise to room temperature
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. extractionThe reaction mixture was then extracted with DCM (3×80 ml)
  5. washthe combined organic extracts washed with brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed under reduced pressure
  8. customto give a solid which
  9. customwas purified by flash chromatography (DCM)

出典と根拠

ORDレコード
ord-bf730d2810124dec845a7553130dedc8
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08895313B2

反応ノート

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