Acetone → HCID 68673189, compound

HRID 1183082Notes

Reaction equation

HRID 1183082 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][N:9]([S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N+:31]([O-:33])=[O:32])(=[O:24])=[O:23])[CH2:10][CH2:11][N:12]1[CH:17]=[CH:16][C:15]2[CH:18]=[CH:19][O:20][C:14]=2[C:13]1=[O:21])(=O)=O.[I-:34].[Na+].CC(C)=O>O>[I:34][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][N:12]1[CH:17]=[CH:16][C:15]2[CH:18]=[CH:19][O:20][C:14]=2[C:13]1=[O:21])[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N+:31]([O-:33])=[O:32])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 86649392HCID 86649392, compound

Product 1

HCID 68673189HCID 68673189, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-{(2-Nitrobenzenesulfonyl)-[2-(7-oxo-7H-furo[2,3-c]pyridin-6-yl)ethyl]amino}propyl methanesulfonate (480 mg, 0.96 mmol) and sodium iodide (720 mg, 4.8 mmol) were added to acetone (20 ml), and heated under reflux for 5 hours. The reaction mixture was cooled to room temperature, water was added, and extraction with dichloromethane was performed. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to thereby obtain 474 mg (yield: 93%) of N-(3-iodopropyl)-2-nitro-N-[2-(7-oxo-7H-furo[2,3-c]pyridin-6-yl)ethyl]benzenesulfonamide as a yellow amorphous solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. extractionextraction with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40a400c5755748ccafe6103490f672c0
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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