Lawesson's reagent → HCID 22246906, compound

HRID 1699065Notes

Reaction equation

HRID 1699065 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) δ63.29 (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-cc3f2d0b7f354422864e5164dfcbb629
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

Loading…