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

HRID 339533

Reaction equation

HRID 339533 reaction equation
[I: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]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:28]=3[N:29]=2)=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C>C1COCC1>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[S:26][C:27]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:28]=4[N:29]=3)=[CH:23][CH:24]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 112085984-Iodo-3-nitrobenzoic acid

Product 1

HCID 673132054-Iodo-3-nitro-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-iodo-3-nitrobenzoic acid (0.286 g, 0.976 mmol) and thionyl chloride (5 ml) was heated under reflux for 3 h. The reaction mixture was cooled to room temperature and the excess reagent and solvent 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-aminophenyl)-6-methoxybenzothiazole (0.25 g, 0.976 mmol) and Hunig's base (0.151 g, 1.17 mmol) in dry THF (10 ml) to give the title compound (0.403 g, 78%) as a yellow solid after work-up.

Workup

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

Sources & evidence

ORD record
ord-84cb27c98a12420a880553ff01b43a91
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Linked notes

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