Lawesson's reagent → 3-Morpholin-4-yl-3-thioxopropanenitrile

HRID 572599Notes

Reaction equation

HRID 572599 reaction equation
[N:1]1([C:7](=O)[CH2:8][C:9]#[N:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1COCC1>[N:1]1([C:7](=[S:21])[CH2:8][C:9]#[N:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 2292794-(Cyanoacetyl)morpholine

Product 1

HCID 451589413-Morpholin-4-yl-3-thioxopropanenitrileYield 131.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-morpholin-4-yl-3-oxopropanenitrile (3.0 g, 19.5 mmol) in anhydrous THF (45 mL) was added Lawesson's reagent (4.2 g, 10.3 mmol). The reaction mixture was allowed to stir at rt for 16 h and was then concentrated to small volume. A solid precipitated and was filtered. The solid was washed with diethyl ether to give 3-morpholin-4-yl-3-thioxopropanenitrile (2.3 g, 70%). LCMS: (AA) ES+ 171.2. 1H NMR (400 MHz, CDCl3) δ: 4.27-4.29 (m, 2H), 4.00 (s, 2H) and 3.81-3.83 (m, 6H).

Workup

  1. concentrationwas then concentrated to small volume
  2. customA solid precipitated
  3. filtrationwas filtered
  4. washThe solid was washed with diethyl ether

Sources & evidence

ORD record
ord-b01eed263b9946928e46ec312b2576dd
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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