Sodium hydride → 2,4-Dichloro-5-(diethylphosphonomethoxymethyl)thiazole

HRID 896001Notes

Reaction equation

HRID 896001 reaction equation
[OH:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[H-].[Na+].[Cl:13][C:14]1[S:15][C:16]([CH2:20]Br)=[C:17]([Cl:19])[N:18]=1>C1COCC1>[Cl:13][C:14]1[S:15][C:16]([CH2:20][O:1][CH2:2][P:3]([O:7][CH2:8][CH3:9])([O:4][CH2:5][CH3:6])=[O:10])=[C:17]([Cl:19])[N:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76513Diethyl phosphonomethanolHCID 22349219358672-75-0

Product 1

HCID 574577912,4-Dichloro-5-(diethylphosphonomethoxymethyl)thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl hydroxymethylphosphonate (1.2 mmol) in THF (10 mL) at 0° C. was added 60% sodium hydride (1.1 mmol) and allowed to stir for 15 minutes before adding 2,4-dichloro-5-(bromomethyl)thiazole (1 mmol). The mixture was warmed to room temperature and allowed to stir for 3 h. The reaction was extracted and chromatographed to yield 2,4-dichloro-5-(diethylphosphonomethoxymethyl)thiazole.

Workup

  1. stirringto stir for 3 h
  2. extractionThe reaction was extracted
  3. customchromatographed

Sources & evidence

ORD record
ord-95422585db3649c6a860a2e3a727a1aa
Source dataset
uspto-grants-2005_07
Patent number
US06919322B2

Reaction notes

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