Thionyl Chloride → 4-Acetoxy-3-nitro-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide

HRID 339519

反応式

HRID 339519 の反応式
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2].S(Cl)(Cl)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[S:29][C:30]3[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:31]=3[N:32]=2)=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[S:29][C:30]4[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:31]=4[N:32]=3)=[CH:26][CH:27]=2)=[O:11])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 140573074-(Acetyloxy)-3-nitrobenzoic acid

生成物 1

HCID 673117154-Acetoxy-3-nitro-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4-acetoxy-3-nitrobenzoic acid (0.44 g, 1.95 mmol) and thionyl chloride (5 ml) was heated under reflux for 1.5 h. The reaction mixture was cooled to room temperature and excess reagent was removed under reduced pressure to give the crude acid chloride. The amide was prepared as described in the Amide Coupling section above using the acid chloride and 2-(4-aminophenyl)-6-methoxybenzothiazole (0.50 g, 1.95 mmol) in dry THF (25 ml) containing diisopropylethylamine (0.302 g, 2.34 mmol) to give the title compound (0.728 g, 86%) as a tan-coloured solid after work-up.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. customexcess 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-aceaf32f8a304220a6ff16ffaa0ed645
出典データセット
uspto-grants-2014_11
特許番号
US08895313B2

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