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Thionyl Chloride → N-[4-(1,3-benzothiazol-2-yl)-3-methoxyphenyl]-4-fluoro-3-nitrobenzamide

HRID 339530
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HRID 339530 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=3[N:29]=2)=[C:21]([O:34][CH3:35])[CH:20]=1.CCN(C(C)C)C(C)C>C1COCC1>[S:26]1[C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=[C:25]1[C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)=[CH:20][C:21]=1[O:34][CH3:35]
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참가 물질

6

반응물 4

HCID 24386Thionyl ChlorideHCID 679874-Fluoro-3-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 672368764-(1,3-Benzothiazol-2-yl)-3-methoxyaniline

생성물 1

HCID 67313096N-[4-(1,3-benzothiazol-2-yl)-3-methoxyphenyl]-4-fluoro-3-nitrobenzamide수율 74%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

A mixture of 4-fluoro-3-nitrobenzoic acid (0.062 g, 0.336 mmol) and thionyl chloride (5 ml) was heated under reflux for 2 h. The reaction mixture was cooled to room temperature and the excess reagent was removed under reduced pressure to give the crude acid chloride. The amide was prepared as described in the Amide Coupling section using the crude acid chloride, 2-(4-amino-2-methoxyphenyl)benzothiazole (0.086 g, 0.336 mmol) and Hunig's base (0.052 g, 0.403 mmol) in dry THF (5 ml) to give the title compound (0.105 g, 74%) as a pale yellow solid after work-up.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. customthe excess reagent was removed under reduced pressure
  4. customto give the crude acid chloride
  5. customThe amide was prepared

출처 및 근거

ORD 기록
ord-020c2bbd05424b598df581324248dafb
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895313B2

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