ChemicalBook CAS DataBase List CYCLOPENTANECARBOTHIOAMIDE

CYCLOPENTANECARBOTHIOAMIDE synthesis

3synthesis methods

Product Name:CYCLOPENTANECARBOTHIOAMIDE
CAS Number:42202-73-3
Molecular formula:C6H11NS
Molecular Weight:129.22

3217-94-5
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Yield:42202-73-3 82%

Reaction Conditions:

with Lawessons reagent in tetrahydrofuran;toluene at 70;

Steps:

5

Intermediate 5; Cyc1opentanecarbothioamide; [00138] Ammonia was bubbled through a solution of cyclopentanecarbonyl chloride (5.46 g, 41.1 mmol) in THF (60 mL) for 30 seconds. After 10 min, the ammonium chloride produced was filtered off and the filtrate concentrated. Then added EtOAc and water and separated the layers and re- extracted with a further portion of EtOAc. The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give the amide (4.46 g, 96%) as a clear oil. The amide (2.60 g, 23.0 mmol) from above was dissolved in THF (60 mL) and Lawesson' s reagent (4.52 g, 11.18 mmol) was added under nitrogen. The mixture was heated at 70 ^SC. After 90 min, toluene was added (30 mL) and heating continued overnight . Then the reaction mixture was concentrated and partitioned between EtOAc and water. The organic layer was concentrated and the residue purified by column chromatography (eluting with EtOAc/Pet ether, 1/1) to give the thioamide (2.44 g, 82%). ¹H NMR: (DMSO) 1.45-1.88 (8H, m) , 2.90 (IH, quin) , 9.13 (IH, br s), 9.32 (IH, br s).

References:

WO2007/117692,2007,A2 Location in patent:Page/Page column 51-52

3400-45-1
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References

4524-93-0
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References