Sodium Carbonate → HCID 18796459, compound

HRID 2396716Notes

Reaction equation

HRID 2396716 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][N:9]=[C:8]([N:11]([CH3:20])[CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:7]=2[CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>Br>[N:14]1([CH2:13][CH2:12][N:11]([CH3:20])[C:8]2[C:7]3[CH:21]=[C:3]([OH:2])[CH:4]=[CH:5][C:6]=3[O:10][N:9]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 18796460HCID 18796460, compound

Product 1

HCID 18796459HCID 18796459, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

5-Methoxy-N-methyl-N-[2-(4-morpholinyl)ethyl]-1,2-benzisoxazol-3-amine (2.6 g) was dissolved in 48% hydrobromic acid (40 ml) and heated to reflux under nitrogen for 6 hours. The reaction was cooled to room temperature, neutralized with saturated Na2CO3 solution, and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. Flash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM provided the pure product (2.1 g), 153°-154° C.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 6 hours
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM

Sources & evidence

ORD record
ord-150dc72684d94abbafe61128e4991232
Source dataset
uspto-grants-1996_02
Patent number
US05494908

Reaction notes

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