Lawesson's reagent → HCID 22246906, compound

HRID 890800Notes

Reaction equation

HRID 890800 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][CH2:7][CH2:8][C:9]([NH2:11])=O)(=[O:4])=[O:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1COCC1>[CH3:1][S:2]([NH:5][CH2:6][CH2:7][CH2:8][C:9]([NH2:11])=[S:21])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 222467414-[(Methylsulfonyl)amino]butanamide

Product 1

HCID 22246906HCID 22246906, compoundYield 149.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-methanesulfonylamino-butyramide (0.50 g, 2.8 mmol) and Lawesson's reagent (0.56 g, 1.4 mmol) in THF (50 mL) was stirred at room temperature for 45 minutes. During this time all of the solid dissolved. The solution was concentrated and purified by flash chromatography (79:1 EtOAc:MeOH) to afford the title compound (0.41 g); 1H NMR (400 MHz, CDCl3) δ 3.29 (s, 3H), 3.07–3.11 (m, 2H), 2.91 (s, 3H), 2.62–2.66 (m, 2H), 1.93–1.99 (m, 2H); MS 197 (M++1).

Workup

  1. dissolutionDuring this time all of the solid dissolved
  2. concentrationThe solution was concentrated
  3. custompurified by flash chromatography (79:1 EtOAc:MeOH)

Sources & evidence

ORD record
ord-02313f0b3ae74096abd671aa63fef175
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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