O-Xylene → Flusulfamide

HRID 2073541Notes

Reaction equation

HRID 2073541 reaction equation
CC1C=CC=CC=1C.[Cl:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH2:12].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][C:22]=1[C:31]([F:34])([F:33])[F:32]>N1C=CC=CC=1>[Cl:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH:12][S:27]([C:24]1[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:31]([F:34])([F:32])[F:33])[CH:23]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 84922-Chloro-4-nitroanilineHCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl Chloride

Product 1

HCID 86268Flusulfamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 400 ml flask, 200 ml of o-xylene, 1 ml of pyridine and 1.7 g (0.01 mole) of 2-chloro-4-nitroaniline were charged. While stirring the contents at room temperature, 2.8 g (0.01 mole) of 4-chloro-3-trifluoromethylbenzenesulfonylchloride was added dropwise at room temperature over 30 minutes. Thereafter, the reaction mixture was heated and stirred for 10 hours under reflux (140°-145° C.). After cooling the reaction mixture to room temperature, it was thoroughly washed first with dilute hydrochloric acid and then with water. Subsequent to its dehydration with anhydrous sodium sulfate, o-xylene was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (eluent: benzene) to isolate the intended Compound 3. m.p. 156°-158° C., yield 2.3 g (55%).

Workup

  1. temperatureThereafter, the reaction mixture was heated
  2. stirringstirred for 10 hours
  3. temperatureunder reflux (140°-145° C.)
  4. temperatureAfter cooling the reaction mixture to room temperature
  5. washit was thoroughly washed first with dilute hydrochloric acid
  6. distillationSubsequent to its dehydration with anhydrous sodium sulfate, o-xylene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c4f49dfaa8074ff7a26a8460b112f3d3
Source dataset
uspto-grants-1990_04
Patent number
US04918106

Reaction notes

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