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

HRID 970156Notes

Reaction equation

HRID 970156 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. At temperatures <30° C., 84 g (174 mmol) of tetrabutylammonium tribromide are then added a little at a time, with vigorous stirring. For work-up, the solid is filtered off with suction and the solution is diluted with methylene chloride and extracted with water. The solvent is stripped off and the residue is then taken up again 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 solution 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-befc2da5e68a4e3cb143032f025dc1a7
Source dataset
uspto-grants-2007_12
Patent number
US07309802B2

Reaction notes

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