Acetic Acid → HCID 13292908, compound

HRID 436823Notes

Reaction equation

HRID 436823 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([NH:5][C:6]1[O:10][N:9]=[C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1)=[O:4].C([O-])(=O)C.[Na+].C(O)(=O)C.[Br:25]Br>C(Cl)Cl>[CH3:1][N:2]([CH3:15])[C:3]([NH:5][C:6]1[O:10][N:9]=[C:8]([C:11]([CH3:12])([CH3:14])[CH3:13])[C:7]=1[Br:25])=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 132928951,1-Dimethyl-3-(5-tert-butyl-4-isoxazolyl)urea

Product 1

HCID 13292908HCID 13292908, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1,1-dimethyl-(3-t-butyl-5-isoxazolyl)-urea (0.70 g), anhydrous sodium acetate (0.30 g) and glacial acetic acid (3.3 ml), bromine (0.53 g) is added dropwise in 10 minutes with ice cooling and stirring and the resultant mixture is stirred for 15 minutes. The reaction mixture is poured into ice water (30 ml) and shaken with methylene chloride. The organic layer is washed with saturated aqueous sodium bicarbonate solution and then water and evaporated to remove the solvent. The residue is recrystallized from benzene to give 1,1-dimethyl-3-(3-t-butyl-4-bromo-5-isoxazolyl)urea (0.96 g) as crystals melting at 175.5° to 176.5° C. (decomp.).

Workup

  1. additionis added dropwise in 10 minutes with ice cooling
  2. washThe organic layer is washed with saturated aqueous sodium bicarbonate solution
  3. customwater and evaporated
  4. customto remove the solvent
  5. customThe residue is recrystallized from benzene

Sources & evidence

ORD record
ord-58ccc35fef7847b69212edd02654e57c
Source dataset
uspto-grants-1977_06
Patent number
US04028376

Reaction notes

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