Nitrogen → HCID 12147024, compound

HRID 1836325Notes

Reaction equation

HRID 1836325 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][CH2:7][N:8]1[C:13]([CH3:14])=[CH:12][N:11]=[C:10](O)[C:9]1=[O:16])=[O:5].P(Br)(Br)([Br:19])=O.N#N.[OH-].[NH4+]>ClCCl.C(Cl)(Cl)Cl.O>[CH3:1][CH2:2][O:3][C:4]([CH2:6][CH2:7][N:8]1[C:13]([CH3:14])=[CH:12][N:11]=[C:10]([Br:19])[C:9]1=[O:16])=[O:5]

Participants

8

Reactant 4

HCID 947NitrogenHCID 14923Ammonium HydroxideHCID 24613Phosphorus oxybromideHCID 178471838HCID 178471838, compound

Product 1

HCID 12147024HCID 12147024, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred slurry of 1-[(2-ethoxycarbonyl)ethyl]-3-hydroxy-6-methylpyrazinone (2-6) (3.8 g, 16.8 mmol) in 20 mL of dichloromethane, phosphorous oxybromide (5.8 g, 20.2 mmol) was added at 50° C. under a steady stream of N2. The resulting mixture was stirred for 2 hours. The reaction mixture was allowed to cool to room temperature and stirring was continued overnight. The mixture was diluted with 30 mL of chloroform and 30 mL of cold water, basified with ammonium hydroxide, and extracted with 30 mL of chloroform (3×). The combined organic layers were dried over anhydrous sodium sulfate, and concentrated in vacuo to yield the title compound (3.8 g, 80%) as an orange solid; the product was verified by NMR. 1H NMR (CDCl3): δ 7.01 (s, 1H), 4.26 (q, 2H), 4.16 (q, 2H), 2.83 (t, 2H), 2.38 (s, 3H), 1.25 (t, 3H).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionextracted with 30 mL of chloroform (3×)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03ed4fefc38d4640afc63327f7c41a09
Source dataset
uspto-grants-2004_08
Patent number
US06777431B2

Reaction notes

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