반응 #87885

반응 방정식

Oxalyl chloride

5-(1-methyl-1H-pyrazol-4-yl)-2-naphthoic acid

guanidine hydrochloride

sodium hydroxide

→

5-(1-methyl-1H-pyrazol-4-yl)-2-naphthoylguanidine

수율 83.2%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added in portions during the reaction to effect dissolution))
2. 2
   온도The reaction mixture was then heated for 1 hour at 40° C.
3. 3
   농축before being concentrated under reduced pressure
4. 4
   workup.STIRRINGthe reaction mixture was then stirred for 30 minutes
5. 5
   기타The organic phase was separated
6. 6
   추출the aqueous phase was extracted with chloroform (3×30 mL)
7. 7
   세척The combined organic extracts were washed sequentially with 1M aqueous sodium hydroxide (60 mL) and water (40 mL)
8. 8
   건조dried (Na2SO4)
9. 9
   농축concentrated in vacuo
10. 10
    기타to give
11. 11
    기타a glassy solid (1.45 g after drying under high vacuum)
12. 12
    workup.DISSOLUTIONThis solid was dissolved in dichloromethane which
13. 13
    기타to evaporate slowly

실험 절차

Oxalyl chloride (1.1 mL, 13 mmol) was added to a solution of 5-(1-methyl-1H-pyrazol-4-yl)-2-naphthoic acid (1.19 g, 4.71 mmol) in anhydrous dichloromethane (200 mL (which was added in portions during the reaction to effect dissolution)) containing dimethylformamide (2 drops) under nitrogen and the mixture was stirred at room temperature for 4.25 hours. The reaction mixture was then heated for 1 hour at 40° C., before being concentrated under reduced pressure. The resulting crude acid chloride was suspended in anhydrous tetrahydrofuran (50 mL) and this mixture was added dropwise to a solution of guanidine hydrochloride (2.09 g, 21.9 mmol) in 2M aqueous sodium hydroxide (15 mL, 30 mmol) and the reaction mixture was then stirred for 30 minutes. The organic phase was separated, and the aqueous phase was extracted with chloroform (3×30 mL) followed by ethyl acetate (3×30 mL). The combined organic extracts were washed sequentially with 1M aqueous sodium hydroxide (60 mL) and water (40 mL), then dried (Na2SO4) and concentrated in vacuo to give a glassy solid (1.45 g after drying under high vacuum). This solid was dissolved in dichloromethane which was then allowed to evaporate slowly to give 5-(1-methyl-1H-pyrazol-4-yl)-2-naphthoylguanidine as a yellow solid (1.15 g, 83%).

출처