Sodium Carbonate → HCID 18796459, compound

HRID 1080425Notes

Reaction equation

HRID 1080425 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-59c02d7efd3b49f6b7b784b7053392ad
Source dataset
uspto-grants-1996_12
Patent number
US05580982

Reaction notes

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