Iodine → Dibutyl[4-[2-(thiophene-2-yl)vinyl]phenyl]amine

HRID 85340Notes

Reaction equation

HRID 85340 reaction equation
C1([Li])C=CC=CC=1.[Cl-].[C:9]1([CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:13][CH:12]=[CH:11][CH:10]=1.[CH2:34]([N:38]([CH2:47][CH2:48][CH2:49][CH3:50])[C:39]1[CH:46]=[CH:45][C:42]([CH:43]=O)=[CH:41][CH:40]=1)[CH2:35][CH2:36][CH3:37].II>C1(C)C=CC=CC=1.O.O1CCCC1>[CH2:34]([N:38]([CH2:47][CH2:48][CH2:49][CH3:50])[C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[CH:14][C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[CH:41][CH:40]=1)[CH2:35][CH2:36][CH3:37]

Participants

8

Reactant 4

HCID 807IodineHCID 6053914-(Dibutylamino)benzaldehydeHCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 178506676HCID 178506676, compound

Product 1

HCID 68008974Dibutyl[4-[2-(thiophene-2-yl)vinyl]phenyl]amineYield 94.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, to 70 ml of tetrahydrofuran was added 10.45 g of phenyllithium (19% solution in dibutylether) (23.6 mmol), and 8.09 g (20.5 mmol) of 2-thenyl triphenylphosphonium chloride was added thereto under cooling. To this mixture was added dropwise 4.92 g (21.0 mmol) of 4-(dibutylamino)benzaldehyde. The mixture was stirred at the same temperature for 1 hour. After the reaction mixture was poured into water, extraction with toluene, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give an orange liquid. This liquid was dissolved in 200 ml of toluene and 200 mg of iodine was added thereto. After stirred at room temperature for 15 minutes, the mixture was added to water and the phases were separated. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 6.09 g of an orange oily matter (yield: 94.8%).

Workup

  1. additionwas added
  2. temperatureunder cooling
  3. washwashing with a saturated saline solution
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration
  5. customThe residue was purified by silica gel column chromatography
  6. customto give an orange liquid
  7. stirringAfter stirred at room temperature for 15 minutes
  8. customthe phases were separated
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography
  12. customto give 6.09 g of an orange oily matter (yield: 94.8%)

Sources & evidence

ORD record
ord-410f12d1564b41fabda73dba90ee31bb
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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