N-Methylethylenediamine → 6-Methoxyl-N-[2-(methylamino)ethyl)-1,2-benzisoxazol-3-amine

HRID 582880Notes

Reaction equation

HRID 582880 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][N:3]=1.[CH3:13][NH:14][CH2:15][CH2:16][NH2:17]>>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([NH:17][CH2:16][CH2:15][NH:14][CH3:13])=[N:3][O:4][C:5]=2[CH:10]=1

Participants

3

Reactant 2

HCID 8014N-MethylethylenediamineHCID 158169243-Chloro-6-methoxy-1,2-benzoxazole

Product 1

HCID 187964466-Methoxyl-N-[2-(methylamino)ethyl)-1,2-benzisoxazol-3-amine

Conditions

Temperature
140 °C

Procedure

To a sealed tube was added 3-chloro-6-methoxy-1,2-benzisoxazole (2.0 g) and N-methylethylenediamine (4.8 g). The reaction was heated to 140° C. over 48 hours and then cooled to room temperature. The residue was partitioned between EtOAc and brine, washed with brine (4×) and the organic phase was dried over MgSO4 and concentrated in vacuo. Flash chromatography (silica gel) eluting with 5% acetone/CH2Cl2 provided a residue upon evaporation (0.4 g) m.p. 136-137° C.

Workup

  1. temperaturecooled to room temperature
  2. customThe residue was partitioned between EtOAc and brine
  3. washwashed with brine (4×)
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography (silica gel) eluting with 5% acetone/CH2Cl2
  7. customprovided a residue
  8. customupon evaporation (0.4 g) m.p. 136-137° C.

Sources & evidence

ORD record
ord-0ccf16cfb8414d058e12e23c334533ee
Source dataset
uspto-grants-1999_07
Patent number
US05925766

Reaction notes

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