Methylhydrazine → HCID 19360031, compound

HRID 376840Notes

Reaction equation

HRID 376840 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(Cl)(O[C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.[CH3:34][NH:35][NH2:36]>ClCCCl>[CH3:34][N:35]([C:26]([NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:32])[NH2:36]

Participants

6

Reactant 4

HCID 6061MethylhydrazineHCID 8471TriethylamineHCID 75899Benzenamine, 2-phenoxy-HCID 94429Triphosgene

Product 1

HCID 19360031HCID 19360031, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Phenoxyaniline (5.57 g) and triethylamine (4.2 mL) were dissolved in 100 mL of 1,2-dichloroethane. Triphosgene (Cl3COC(=O)OCCl3, 2.97 g) was added and a precipitate formed. The mixture was heated to reflux and the solid redissolved. After 5.5 h, the solution was cooled and 1.6 mL of methyl hydrazine was added and a new precipitate formed. The mixture was stirred at room temperature overnight. The solvent was removed and the residue was partitioned between ethyl acetate and 1N aqueous HCl solution. The organic phases were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (1:1 hexane:ethyl acetate as eluant). The second-least polar component was collected, the eluant was removed under reduced pressure, and the residue was triturated with hexane to afford 3.86 g (50%) of the title compound of Step A, m.p. 117-119° C.

Workup

  1. customa precipitate formed
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. dissolutionthe solid redissolved
  5. temperaturethe solution was cooled
  6. customa new precipitate formed
  7. customThe solvent was removed
  8. customthe residue was partitioned between ethyl acetate and 1N aqueous HCl solution
  9. dry with materialThe organic phases were dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by flash chromatography (1:1 hexane:ethyl acetate as eluant)
  13. customThe second-least polar component was collected
  14. customthe eluant was removed under reduced pressure
  15. customthe residue was triturated with hexane

Sources & evidence

ORD record
ord-c23b8221ef1a4be5a750d04e72ad9f10
Source dataset
uspto-grants-2000_02
Patent number
US06022870

Reaction notes

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