Diethylhydroxylamine → 2-[5-(N,N-diethylaminooxycarbonylmethylthio)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

HRID 128901

Reaction equation

HRID 128901 reaction equation
[C:1]([CH2:4][S:5][C:6]1[C:7]([Cl:24])=[CH:8][C:9]([F:23])=[C:10]([N:12]2[C:20](=[O:21])[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13]2=[O:22])[CH:11]=1)([OH:3])=[O:2].[CH2:25]([N:27]([CH2:29][CH3:30])O)[CH3:26]>O1CCCC1>[CH2:25]([N:27]([O:2][C:1]([CH2:4][S:5][C:6]1[C:7]([Cl:24])=[CH:8][C:9]([F:23])=[C:10]([N:12]2[C:20](=[O:21])[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13]2=[O:22])[CH:11]=1)=[O:3])[CH2:29][CH3:30])[CH3:26]

Participants

4

Reactant 2

HCID 19463DiethylhydroxylamineHCID 134544942-(5-carboxymethylthio-4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

Product 1

HCID 571677982-[5-(N,N-diethylaminooxycarbonylmethylthio)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dioneYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of tetrahydrofuran, 1.85 g of 2-(5-carboxymethylthio-4-chloro -2-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione was dissolved, to which 0.97 g of N,N'-carbonyldiimidazole was added and the resultant mixture was stirred for 30 minutes at room temperature. To the resultant mixture, 0.53 g of N,N-diethylhydroxylamine was added, and the resultant mixture was stirred for 2 hours at room temperature. After completion of the reaction, the reaction mixture was poured into a saturated saline solution and extracted with ethyl acetate. The extract was washed with a saturated saline solution, dried with anhydrous magnesium sulfate, and evaporated to remove the solvent under reduced pressure. The residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=5:1 to 3:1), which afforded 1.60 g of 2-[5-(N,N-diethylaminooxycarbonylmethylthio)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. additionthe reaction mixture was poured into a saturated saline solution
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure
  9. customThe residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=5:1 to 3:1), which

Sources & evidence

ORD record
ord-ef54eb675b9041be86bab5c4850f5a93
Source dataset
uspto-grants-1995_11
Patent number
US05466663

Linked notes

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