Potassium Carbonate → Benzenamine, 4-bromo-2-(4,5-dihydro-3-isoxazolyl)-3-methyl-

HRID 49671

Reaction equation

HRID 49671 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[Br-:20].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[Br:20][C:11]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:3]2[CH2:4][CH2:5][O:1][N:2]=2)[C:12]=1[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97940062-(4,5-Dihydroisoxazol-3-yl)-3-methylanilineHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 9813747Benzenamine, 4-bromo-2-(4,5-dihydro-3-isoxazolyl)-3-methyl-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

30 g (170 mmol) of 2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline are dissolved in 400 ml of acetonitrile, and 94 g (0.68 mol) of potassium carbonate are added. 84 g (174 mmol) of tetrabutylammonium tribromide are subsequently added a little at a time with vigorous stirring at temperatures <30° C. For work-up, the solid is filtered off with suction and the filtrate is diluted with methylene chloride and extracted with water. The solvent is stripped off and the residue is again taken up in methyl tert-butyl ether and washed twice with water. The organic phase is dried and concentrated.

Workup

  1. filtrationFor work-up, the solid is filtered off with suction
  2. additionthe filtrate is diluted with methylene chloride
  3. extractionextracted with water
  4. washwashed twice with water
  5. customThe organic phase is dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-02667dfd44af4d04b87c7f70c42c468f
Source dataset
uspto-grants-2004_03
Patent number
US06706886B2

Linked notes

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