تفاعل #87888

معادلة التفاعل

Oxalyl chloride

2,3-methylenedioxycinnamic acid

guanidine hydrochloride

dimethylformamide

→

crude product

المردود 66.0%

2,3-Methylenedioxycinnamoylguanidine

المردود 66.0%

المذيبات

dichloromethane

chloroform

sodium hydroxide

ظروف التفاعل

المعالجة

1. 1
   أخرىthe resulting solution was evaporated to dryness under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in dry tetrahydrofuran (5 mL)
3. 3
   workup.STIRRINGThe reaction was stirred at room temperature for 1 hour
4. 4
   ترشيحThe resulting precipitate of crude product (100 mg) was collected by filtration
5. 5
   استخلاصThe filtrate was extracted with chloroform (3×30 mL) and ethyl acetate (20 mL)
6. 6
   غسيلThe combined organic extracts were washed with 2M aqueous sodium hydroxide (20 mL), water (20 mL)
7. 7
   تجفيفdried (Na2SO4)
8. 8
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

Oxalyl chloride (0.68 mL, 7.8 mmol) was added to a suspension of 2,3-methylenedioxycinnamic acid (500 mg, 2.6 mmol) in dichloromethane (5 mL) containing a drop of dimethylformamide. The mixture was stirred for 2.5 hours and the resulting solution was evaporated to dryness under reduced pressure. The residue was dissolved in dry tetrahydrofuran (5 mL) and added to a solution of guanidine hydrochloride (1.24 g, 13 mmol) in 2M aqueous sodium hydroxide (8 mL). The reaction was stirred at room temperature for 1 hour and chloroform was then added. The resulting precipitate of crude product (100 mg) was collected by filtration. The filtrate was extracted with chloroform (3×30 mL) and ethyl acetate (20 mL). The combined organic extracts were washed with 2M aqueous sodium hydroxide (20 mL), water (20 mL), dried (Na2SO4) and concentrated under reduced pressure to give a further quantity of crude product (400 mg). The two crops of crude product were combined, suspended in chloroform (10 mL) and stirred vigorously for 20 minutes. The resulting 2,3-methylenedioxycinnamoylguanidine (420 mg) was collected by filtration and dried under vacuum.

المصدر