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

HRID 339519

Reaction equation

HRID 339519 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aceaf32f8a304220a6ff16ffaa0ed645
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Linked notes

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