Pyridine → 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl methoxy(methyl)carbamate

HRID 2424321Notes

Reaction equation

HRID 2424321 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]2[CH2:18][CH2:17]2)=[C:4]([OH:19])[CH:3]=1.N1C=CC=CC=1.[C:26](Cl)(Cl)=[O:27].C1(C)C=CC=CC=1.Cl.[CH3:38][NH:39][O:40][CH3:41]>O.C1(C)C=CC=CC=1>[CH3:41][O:40][N:39]([CH3:38])[C:26](=[O:27])[O:19][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[O:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH:16]1[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 19083224Phosgen tolueneHCID 178424441HCID 178424441, compound

Product 1

HCID 229401746-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl methoxy(methyl)carbamateYield 38.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

200 mg (0.722 mmol) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was mixed with toluene (3 mL) and the mixture was ice-cooled. To the mixture were added 60 ìL (0.742 mmol) of pyridine, then 0.67 mL (0.724 mmol) of 1.08 mol/L phosgene-toluene solution under nitrogen atmosphere with stirring, and the resulting mixture was stirred at room temperature for 15 minutes. The reaction mixture was ice-cooled, 120 ìL (1.48 mmol) of pyridine, then 70.4 mg (0.722 mmol) of N,O-dimethylhydroxylamine hydrochloride were added to the mixture, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane: ethyl acetate, gradient) to obtain 100 mg (0.275 mmol, Yield: 38.1%) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl methoxy(methyl)carbamate (Compound No. 3564).

Workup

  1. temperaturecooled
  2. temperaturecooled
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed
  8. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane: ethyl acetate, gradient)

Sources & evidence

ORD record
ord-b71b4d90f4274a5ca79886a96b2655a0
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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