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

HRID 339530Notes

Reaction equation

HRID 339530 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-020c2bbd05424b598df581324248dafb
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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