Triethylamine → N-3-thienylpentanamide

HRID 1715218Notes

Reaction equation

HRID 1715218 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([NH2:6])=[CH:2]1.C(N(CC)CC)C.[C:14](Cl)(=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18]>ClCCl>[S:1]1[CH:5]=[CH:4][C:3]([NH:6][C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 640543Thiophen-3-amine

Product 1

HCID 66725662N-3-thienylpentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of thiophen-3-amine (see Galvez, C., et al, J. Heterocycl. Chem. (1984), 21:393-5) (5.70 g, 57.0 mmol) and triethylamine (5.82 g, 58.0 mmol) in dichloromethane (100 mL) was added pentanoyl chloride (6.93 g, 57.0 mmol) dropwise at 0° C. The reaction mixture was stirred at ambient temperature overnight and quenched with water (50.0 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to afford the title compound: MS (ES+) m/z 184.3 (M+1).

Workup

  1. customquenched with water (50.0 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-116543f76a72436aace2cef426c30409
Source dataset
uspto-grants-2010_09
Patent number
US07799798B2

Reaction notes

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