Lawesson's reagent → HCID 22246906, compound

HRID 1595895Notes

Reaction equation

HRID 1595895 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-54ce1e7f4a1e49f0b3b09b54c7d81e53
Source dataset
uspto-grants-2001_09
Patent number
US06288120B1

Reaction notes

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