Lawesson's reagent → HCID 18726778, compound

HRID 842692Notes

Reaction equation

HRID 842692 reaction equation
COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:10]2)=CC=1.[Cl:23][C:24]1[C:25]([NH:39][C:40](=O)[CH2:41][O:42][CH3:43])=[C:26]2[C:31](=[CH:32][C:33]=1[CH3:34])[N:30]=[C:29]([O:35][CH3:36])[C:28]([O:37][CH3:38])=[N:27]2>O1CCCC1>[Cl:23][C:24]1[C:25]([NH:39][C:40](=[S:10])[CH2:41][O:42][CH3:43])=[C:26]2[C:31](=[CH:32][C:33]=1[CH3:34])[N:30]=[C:29]([O:35][CH3:36])[C:28]([O:37][CH3:38])=[N:27]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22614853HCID 22614853, compound

Product 1

HCID 18726778HCID 18726778, compoundYield 145%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-bis(4-Methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (Lawesson's reagent) (4.47 g, 11.06 mmol) was added to 6-chloro-2,3-dimethoxy-5-methoxyacetamido-7-methylquinoxaline (6 g, 18.43 mmol) in tetrahydrofuran (120 mL) and the mixture stirred for 18 hours, then evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using hexane:dichloromethane (1:1 changing to 1:4 changing to 0:1, by volume) to give 6-chloro-2,3-dimethoxy-5-methoxythioacetamido-7-methylquinoxaline (5.48 g, 87%) as a yellow foam, mp 174-176° C.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel, by gradient elution

Sources & evidence

ORD record
ord-86693473d200402c9ddece8b39f73cb8
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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