Hydrazine hydrate (1:1) → HCID 22915358, compound

HRID 1377826Notes

Reaction equation

HRID 1377826 reaction equation
[CH3:1][C:2]1([C:7]2O[C:10]([CH2:12][CH2:13][CH2:14][O:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([C:23]#[N:24])=[CH:18][C:17]=3[CH3:25])=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.CC1(C)OO1.O.[NH2:32][NH2:33]>CC(C)=O.CO>[CH3:1][C:2]1([C:7]2[N:33]=[N:32][C:10]([CH2:12][CH2:13][CH2:14][O:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([C:23]#[N:24])=[CH:18][C:17]=3[CH3:25])=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 115197DimethyldioxiraneHCID 10315262HCID 10315262, compound

Product 1

HCID 22915358HCID 22915358, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 3c, 5-(2-methyl-1,3-dioxolan-2-yl)-2-[3-(2,6-dimethyl-4-cyanophenoxy)-propyl]furan; (1.05 g; 3.08 mmol), 48 mL (0.06M) of dimethyldioxirane in acetone, and 10 mL of acetone were reacted. The resulting product was disolved in methanol and reacted with 85% hydrazine hydrate (0.15 mL; 4.49 mmol) then purified by chromatography on silica gel with 65% ethyl acetate/hexane to afford 0.511 g (47%) of 6-(2-methyl-1,3-dioxolan-2-yl)-3-[3-(2,6-dimethyl-4-cyanophenoxy)propyl]-pyridazine.

Workup

  1. customthen purified by chromatography on silica gel with 65% ethyl acetate/hexane

Sources & evidence

ORD record
ord-db9691eb911f4f348150e751426bf283
Source dataset
uspto-grants-1997_09
Patent number
US05665763

Reaction notes

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