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

HRID 339530
ノート
印刷プレビュー

反応式

HRID 339530 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-020c2bbd05424b598df581324248dafb
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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