Methylhydrazine → 4-(Aminomethyl)-3-cyclopropyl-1,2,4-oxadiazole

HRID 351826

Reaction equation

HRID 351826 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7](CN3C(=O)C4=CC=CC=C4C3=O)[O:6][N:5]=2)[CH2:3][CH2:2]1.[CH3:21][NH:22]N>ClCCCl>[NH2:22][CH2:21][N:8]1[CH2:7][O:6][N:5]=[C:4]1[CH:1]1[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 22713498N-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]phthalimide

Product 1

HCID 227134904-(Aminomethyl)-3-cyclopropyl-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-[(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]phthalimide (104 g, 387 mmol) was dissolved in 1,2-dichloroethane (500 mL), N-methylhydrazine (22.4 mL, 426 mmol) was added and the solution was refluxed for 5 h. The suspension was cooled in ice, the precipitate (2-methyl-2,3-dihydro-phthalazine-1,4-dione) was filtered off and washed with 1,2-dichloroethane (100 mL). The filtrate was evaporated and the residue distilled at 70° C./0.4 mbar (bath-T 100-150° C). Yield: 39.3 g (73%). m/z 139 (M).

Workup

  1. temperaturethe solution was refluxed for 5 h
  2. temperatureThe suspension was cooled in ice
  3. filtrationthe precipitate (2-methyl-2,3-dihydro-phthalazine-1,4-dione) was filtered off
  4. washwashed with 1,2-dichloroethane (100 mL)
  5. customThe filtrate was evaporated
  6. distillationthe residue distilled at 70° C./0.4 mbar (bath-T 100-150° C)

Sources & evidence

ORD record
ord-690efa1200264a80a13c5dfe52644e48
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Linked notes

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