Oxalyl chloride → 4-pentyl-4H-thieno[3,2-b]pyrrole-5,6-dione

HRID 1715220Notes

Reaction equation

HRID 1715220 reaction equation
[CH2:1]([NH:6][C:7]1[CH:11]=[CH:10][S:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:12](Cl)(=[O:16])[C:13](Cl)=[O:14]>CCOCC>[CH2:1]([N:6]1[C:13](=[O:14])[C:12](=[O:16])[C:8]2[S:9][CH:10]=[CH:11][C:7]1=2)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 65438924N-pentylthiophen-3-amine

Product 1

HCID 667254144-pentyl-4H-thieno[3,2-b]pyrrole-5,6-dioneYield 531.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of N-pentylthiophen-3-amine (7.30 g, 4.30 mmol) in ether (50.0 mL) was added a solution of oxalyl chloride (6.00 mL, 42.0 mmol) in ether (50.0 mL) slowly at −10° C. The reaction mixture was stirred at ambient temperature for 3 h and quenched with cold water. The organic layer was separated, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography to afford the title compound (5.10 g, 53%): MS (ES+) m/z 246.3 (M+23).

Workup

  1. customquenched with cold water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-89ce2bd112694491abdf48f30b63cc32
Source dataset
uspto-grants-2010_09
Patent number
US07799798B2

Reaction notes

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