Potassium Carbonate → HCID 19871098, compound

HRID 329594Notes

Reaction equation

HRID 329594 reaction equation
Cl.[CH3:2][NH:3][OH:4].C(=O)([O-])[O-].[K+].[K+].[Br:11][CH:12]([CH:16](Br)[CH3:17])[C:13](Cl)=[O:14]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:11][CH:12]1[CH:16]([CH3:17])[O:4][N:3]([CH3:2])[C:13]1=[O:14]

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 77906N-methylhydroxylamine hydrochlorideHCID 53871009HCID 53871009, compound

Product 1

HCID 19871098HCID 19871098, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 12.5 g (150 mmol) of N-methylhydroxylamine hydrochloride, 20.7 g (150 mmol) of potassium carbonate and 4.1 g (15 mmol) of tetrabutylammonium hydrogen sulfate in 250 ml of methylene chloride, there was added 2, 3-dibromobutyryl chloride (42 g,150 mmol) followed by the addition of 41.4 g (300 mmol) of potassium carbonate. After three days the mixture was filtered, the filtrate was concentrated and the concentrate was chromatographed on silica gel with 40% ethyl acetate-hexane to afford 16.8 g (86 mmol, 57%) of 4-bromo-2,5-dimethyl-3-isoxazolidinone.

Workup

  1. filtrationAfter three days the mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe concentrate was chromatographed on silica gel with 40% ethyl acetate-hexane

Sources & evidence

ORD record
ord-11760dc19e9145b2a47032ce35f838be
Source dataset
uspto-grants-1990_01
Patent number
US04892870

Reaction notes

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