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

HRID 339489
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HRID 339489 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 10942334Sodium MethoxideHCID 13599215Diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate

생성물 1

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

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bf730d2810124dec845a7553130dedc8
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895313B2

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