Trifluoroacetic acid → HCID 22598374, compound

HRID 1760331Notes

Reaction equation

HRID 1760331 reaction equation
C(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].F[C:10](F)(F)[C:11](O)=O.[NH2:16][C:17]1[CH:21]=[CH:20][S:19][CH:18]=1.[OH-].[Na+]>ClCCl.O.C(OCC)C>[CH2:7]([N:16]1[C:17]2=[CH:21][CH2:20][S:19][C:18]2=[CH:17][C:18]2[S:19][CH:20]=[CH:10][C:11]1=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH3:2]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 8130HeptanalHCID 14798Sodium HydroxideHCID 640543Thiophen-3-amine

Product 1

HCID 22598374HCID 22598374, compoundYield 238.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of heptanal (0.59 g, 5.16 mmol) and trifluoroacetic acid (100 mg) in anhydrous dichloromethane (50 mL) was added dropwise to a solution of 3-aminothiophene (0.93 g, 9.38 mmol) in anhydrous dichloromethane (50 mL) at −5° C. The reaction mixture was stirred at room temperature for 1.5 h. Trifluoroacetic acid (1.07 g, 9.38 mmol) was added and the reaction mixture was then heated at reflux for 6 h. The solution was cooled and diethyl ether (150 mL) and water (30 mL) were added. The aqueous layer was basified with 0.5 N aqueous sodium hydroxide solution. The organic layer was separated. The aqueous layer was again extracted into diethyl ether (150 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography (eluent: 90% petroleum ether 80-100/10% dichloromethane to 100% dichloromethane) afforded 4-hexyldithieno[3,2-b:2′3′-e]pyridine (0.58 g, 45%) as a red oil: δH(CDCl3, 250 MHz) 7.75 (2H, d, 3JHH=6 Hz), 7.59 (2H, d, 3JHH=6 Hz), 3.16 (2H, t, 3JHH=8 Hz), 1.90 (2H, m), 1.27-1.49 (6H, m), 0.89 (3H, t, 3JHH=7 Hz); δC(CDCl3, 63 MHz) 156.2, 140.4, 130.7, 129.7, 34.8, 31.9, 29.8, 28.3, 22.9, 14.4.

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureat reflux for 6 h
  3. temperatureThe solution was cooled
  4. customThe organic layer was separated
  5. extractionThe aqueous layer was again extracted into diethyl ether (150 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (eluent: 90% petroleum ether 80-100/10% dichloromethane to 100% dichloromethane)

Sources & evidence

ORD record
ord-dcd0e9e1dbc94649bf698d2c499e2aa4
Source dataset
uspto-grants-2005_01
Patent number
US06841677B2

Reaction notes

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