Chloromethyl Methyl Ether → HCID 19595239, compound

HRID 612457Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][NH:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:19]OC[Cl:22].[OH-].[Na+]>C(O)(=O)C>[ClH:22].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[CH2:19][N:11]([NH:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH2:10][CH2:9]2

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (0.55 g) was added portionwise to a suspension of N-[2-(3-methoxyphenyl)ethylidene]-N'-pyridin-4-yl hydrazone (2.0 g) in tetrahydrofuran (36 ml) at 0° C. The reaction mixture was stirred at ambient temperature for 1 hr, sodium sulfate decahydrate was added. The mixture was filtered, and the filtrate was concentrated to give 1.73 g of N-[2-(3-methoxyphenyl)ethyl]-N'-pyridin-4-yl hydrazine. A solution of N-[2-(3-methoxyphenyl)ethyl]-N'-pyridin-4-yl hydrazine (0.85 g) and chloromethyl methyl ether (0.31 g) in acetic acid (15 ml) was heated at 55° C. for 1.5 hrs, and the mixture was cooled to 0° C. Sodium hydroxide solution (15%) was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in methanol and methanolic hydrogen chloride and then ether were added to give 0.31 g (30%) of product, mp 199-200° C.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe combined organic extracts were washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated
dissolutionThe residue was dissolved in methanol
additionmethanolic hydrogen chloride and then ether were added

Sources & evidence

ORD record: ord-85e364b70a7742a2b0b61c01bdd7697e
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06004977

Reaction notes

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