Dichloromethane → HCID 19871100, compound

HRID 329595

Reaction equation

HRID 329595 reaction equation
C(O)(=O)C(O)=O.[CH:7]([NH:10][OH:11])([CH3:9])[CH3:8].[OH-].[Na+].[Br:14][CH:15]([CH2:19]Br)[C:16](Cl)=[O:17].C(Cl)Cl>O>[Br:14][CH:15]1[CH2:19][O:11][N:10]([CH:7]([CH3:9])[CH3:8])[C:16]1=[O:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium Hydroxide3×HCID 867902,3-Dibromopropanoyl chlorideHCID 19871111N-Isopropylhydroxylamineoxalate

Product 1

HCID 19871100HCID 19871100, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 6 g (25 mmol) of N-isopropylhydroxylamine oxalate and 1N sodium hydroxide (50 ml) in water (100 ml) cooled to 0° C. there was added 2,3-dibromopropionyl chloride (12.5 g, 50 mmol), followed by the addition of 50 ml of 1N sodium hydroxide. Ten minutes later, 150 ml of methylene chloride and 60 ml of 1N sodium hydroxide were added. The mixture was stirred continuously for one hours following which the organic phase was separated, dried over anhydrous magnesium sulfate and concentrated. The concentrate was chromatographed on silica gel with 40% ethyl acetatehexane to afford 3.3 g of 4-bromo-2-isopropyl-3-isoxazolidinone.

Workup

  1. customwas separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe concentrate was chromatographed on silica gel with 40% ethyl acetatehexane

Sources & evidence

ORD record
ord-730eb489b9ec4f098361805efb92dc25
Source dataset
uspto-grants-1990_01
Patent number
US04892870

Linked notes

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