Carbon Tetrachloride → HCID 66941854, compound

HRID 348727Notes

Reaction equation

HRID 348727 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([CH3:15])=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2].Br[N:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23].N([C:31]([CH3:35])([CH3:34])C#N)=NC(C)(C)C#N.[C:36](Cl)(Cl)(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][N:17]3[C:21](=[O:22])[C:20]4[C:19](=[CH:36][CH:35]=[CH:31][CH:34]=4)[C:18]3=[O:23])=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 13527238HCID 13527238, compound

Product 1

HCID 66941854HCID 66941854, compound

Procedure

In carbon tetrachloride (100 ml), 5-methyl-benzo[b]thiophene-2-carboxylic acid ethyl ester (2.36 g) prepared by the method described in PCT Patent WO 0153291 was dissolved. The solution was added with N-bromosuccinimide (2.00 g) and azobisisobutyronitrile (140.7 mg), and the whole was stirred for 17 hours under thermal reflux. After the insoluble matter had been removed through filtration, the residue was recrystallized with methanol. Then, the crystal was dissolved in DMF (20 ml) and then added with potassium phthalimide (1.18 g), followed by stirring overnight at room temperature. After the solvent had been distilled off, the residue was added with water and extracted with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate, thereby obtaining the subject compound (1.15 g) as a pale-yellow solid.

Workup

  1. dissolutionwas dissolved
  2. customAfter the insoluble matter had been removed through filtration
  3. customthe residue was recrystallized with methanol
  4. dissolutionThen, the crystal was dissolved in DMF (20 ml)
  5. additionadded with potassium phthalimide (1.18 g)
  6. stirringby stirring overnight at room temperature
  7. distillationAfter the solvent had been distilled off
  8. additionthe residue was added with water
  9. extractionextracted with chloroform
  10. washThe organic layer was washed with saturated saline solution
  11. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-09afd769c87541cb8998e08786bb584e
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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