Ethanol → [3-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]propylamino]Guanidine Diacetate

2-[2-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]ethyl-1-methylene]hydrazinecarboximidamide acetate: A mixture of aminoguanidine hydrochloride (0.811 g, 7.33 mmol) and 3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propionaldehyde (1.28 g, 3.66 mmol, prepared in the preceding step) in ethanol (30 mL) was stirred overnight at ambient temperature. The mixture was concentrated in vacuo to approximately 15 mL, then dichloromethane (60 mL) was added to precipitate excess aminoguanidine hydrochloride. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane (30 mL) and extracted with aqueous NaOH (1.85 mL of 2N NaOH in 90 mL water). The aqueous layer was extracted with CH2Cl2 (2×30 mL). The combined organic extracts were washed with water (50 mL) and brine (2×50 mL), dried over K2CO3, filtered, and evaporated to give the free base of the title compound (1.38 g, 93%) as a gold foam.

1. concentrationThe mixture was concentrated in vacuo to approximately 15 mL
2. additiondichloromethane (60 mL) was added
3. customto precipitate excess aminoguanidine hydrochloride
4. filtrationThe mixture was filtered
5. concentrationthe filtrate was concentrated
6. dissolutionThe residue was dissolved in dichloromethane (30 mL)
7. extractionextracted with aqueous NaOH (1.85 mL of 2N NaOH in 90 mL water)
8. extractionThe aqueous layer was extracted with CH2Cl2 (2×30 mL)
9. washThe combined organic extracts were washed with water (50 mL) and brine (2×50 mL)
10. dry with materialdried over K2CO3
11. filtrationfiltered
12. customevaporated

ORD record

ord-d1381f49c99c433385a26c80862856d1

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06638931B1