Reacción #69073

Ecuación de reacción

acetic acid

4-aminobutanol

3-benzoyloxybenzenesulfonyl chloride

DBU

→

title compound

3-(cyclopropylmethoxy)-N-(4-(methoxymethoxy)butyl)benzenesulfonamide

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroobtained
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 10 minutes
3. 3
   ConcentraciónThe reaction mixture was then concentrated under reduced pressure
4. 4
   OtroThe residue was purified by silica gel column chromatography (100% ethyl acetate)
5. 5
   workup.DISSOLUTIONThe obtained colorless oil (147 mg) was dissolved in DMF (4.0 mL)
6. 6
   workup.ADDITIONTo the solution, potassium carbonate (141 mg), potassium iodide (8.5 mg), and (chloromethyl)cyclopropane (47 μL) were added
7. 7
   workup.STIRRINGthe mixture was stirred at 90° C. for 14 hours
8. 8
   TemperaturaThe reaction mixture was cooled to room temperature
9. 9
   workup.ADDITIONwater (10 mL) was then added
10. 10
    Extracciónthe resultant mixture was then extracted with ethyl acetate (10 mL)
11. 11
    LavadoThe organic layer was washed with water (10 mL) and brine (10 mL)
12. 12
    Secadodried over anhydrous sodium sulfate
13. 13
    Concentraciónconcentrated under reduced pressure
14. 14
    OtroThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Procedimiento

A colorless oil (285 mg) was obtained according to the method of Reference Example 233 from 4-aminobutanol (89 mg) and 3-benzoyloxybenzenesulfonyl chloride (300 mg) obtained according to a method described in the document (J. Pesticide. Chem., 13, 107-115 (1988)). This oil was dissolved in methanol (5.0 mL). To the solution, DBU (441 mg) was added, and the mixture was stirred at room temperature for 45 minutes. To the reaction mixture, acetic acid (210 μL) was added, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100% ethyl acetate). The obtained colorless oil (147 mg) was dissolved in DMF (4.0 mL). To the solution, potassium carbonate (141 mg), potassium iodide (8.5 mg), and (chloromethyl)cyclopropane (47 μL) were added, and the mixture was stirred at 90° C. for 14 hours. The reaction mixture was cooled to room temperature, water (10 mL) was then added thereto, and the resultant mixture was then extracted with ethyl acetate (10 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to obtain the title compound (91 mg) as a colorless oil.

Fuente