Pyridine → O-propionyldibromoformaldoxime

HRID 1638353Notes

Reaction equation

HRID 1638353 reaction equation
[Br:1][C:2]([Br:5])=[N:3][OH:4].[C:6](Cl)(=[O:9])[CH2:7][CH3:8].N1C=CC=CC=1>C(Cl)Cl>[C:6]([O:4][N:3]=[C:2]([Br:5])[Br:1])(=[O:9])[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromide

Product 1

HCID 19842362O-propionyldibromoformaldoximeYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the mixture of dibromoformaldoxime (5 g, 24.63 mole) and propionyl chloride (2.31 g, 25 mole) in dry methylene chloride (30 ml) is slowly added dry pyridine (2 g, 25.5 mole) over 10 min at 0° to 5° C. with stirring. After addition the reaction mixture is stirred at 5° C. for 30 min and at 25° C. for another 30 min. The resultant suspension is diluted with methylene chloride and washed with water and brine. The organic layer is dried over MgSO4. Evaporation of solvent affords 5.44 g (85% of theory) of O-propionyldibromoformaldoxime as a light yellow liquid. NMR spectrum shows this to be the desired compound.

Workup

  1. additionAfter addition the reaction mixture
  2. stirringis stirred at 5° C. for 30 min and at 25° C. for another 30 min
  3. washwashed with water and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-3794c5531ae8434b9b3297f2bef27b39
Source dataset
uspto-grants-1989_11
Patent number
US04879314

Reaction notes

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