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4-Nitrophenol → Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid 4-nitrophenyl ester

HRID 427292
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HRID 427292 반응식
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[S:11][C:7]=2[C:6]([C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1.[CH:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21](O)[CH:20]=1.CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[N+:25]([C:24]1[CH:19]=[CH:20][C:21]([O:17][C:16]([C:6]2[C:7]3[S:11][C:10]([C:12]([F:13])([F:14])[F:15])=[N:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:18])=[CH:22][CH:23]=1)([O-:27])=[O:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 9804-NitrophenolHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183569954-Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid

생성물 1

HCID 69689660Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid 4-nitrophenyl ester수율 74.6%

시약·촉매·용매

1
HCID 6344Dichloromethane용매

실험 절차

A suspension of 4-methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid (140 mg) in dichloromethane (10ml) was treated with p-nitrophenol (72 mg), dimethylaminopyridine (catalytic) and 1-(3-dimethylaminopropyl)-3-ethyl carbodimide hydrochloride (150 mg). The mixture was stirred at room temperature for 12 hours and the reaction washed with water (10 ml). The organic layer was separated, dried over magnesium sulphate (5 g) and evaporated in vacuo. Purification by flash chromatography (eluent 50% ethyl acetate/hexane) yielded the title compound as an off-white solid (150 mg). TLC Rf 0.13 (50% ethyl acetate in heptane).

후처리

  1. washthe reaction washed with water (10 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate (5 g)
  4. customevaporated in vacuo
  5. customPurification by flash chromatography (eluent 50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-4a57574299c14853ba29b6f739adcca7
출처 데이터셋
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06313116B1

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