Lawesson's reagent → HCID 22246906, compound

HRID 1955037Notes

Reaction equation

HRID 1955037 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 of Step C (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-bf39fbe144e64b72b6bb737e61dd2f95
Source dataset
uspto-grants-2000_09
Patent number
US06124314

Reaction notes

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