تفاعل #1868315

معادلة التفاعل

4-aminobenzamidine dihydrochloride

succinic anhydride

DMF

HCl

→

title compound

4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid, monohydrochloride

المذيبات

acetone

pyridine

acetone

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added all at once
2. 2
   درجة الحرارةmaintained at 100° C. for 1.5 h
3. 3
   درجة الحرارةAfter cooling to 0° C.
4. 4
   درجة الحرارةwhile maintaining the temperature at 0° C
5. 5
   ترشيحthe solids were collected by vacuum filtration
6. 6
   غسيلThe solids were then washed twice each with aq 0.5M HCl
7. 7
   أخرىwere dried in a vacuum oven at 30°-40° C.
8. 8
   أخرىto afford

الإجراء التجريبي

A mixture of 2.2 g of 4-aminobenzamidine dihydrochloride, 1.1 g of succinic anhydride and 10 mL of DMF was stirred at ambient temperature for 15 min at which time 0.83 mL of pyridine was added all at once. The resulting heterogeneous mixture was warmed to 100° C. and maintained at 100° C. for 1.5 h. The disappearance of starting material was monitored by an in-process check using HPLC Method B. After cooling to 0° C., a solution of 8 wt % concentrated HCl in acetone was added slowly while maintaining the temperature at 0° C. After the addition of additional acetone, the resulting milky suspension was stirred for 30 min and the solids were collected by vacuum filtration. The solids were then washed twice each with aq 0.5M HCl followed by acetone and were dried in a vacuum oven at 30°-40° C. to afford 2.4 g (88% molar yield) of the title compound. Acceptance testing was performed on the product using HPLC Method B to determine the presence of the title product. λmax (CH3OH) 281 nm; (0.1% H3PO4 in water) 203, 270 nm; IR (KBr): 1736 (C=O), 1674 (C--N, C=N), 1599 (C=N) cm-1 ; DSC endotherms at 167° C. and 275° C.; 1H NMR: (d6 -DMSO) δ 12.15 (s, 1H), 10.55 (s, 1H), 9.23 (s, 2H), 9.0 (s, 2H), 7.81 (s, 4H), 3.31 (s, 3H), 2.62 (m, 2H), 2.55 (m, 2H) ppm; 13C NMR: δ 173.6, 171.0, 164.8, 144.3, 129.1, 121.2, 118.3, 31.2, 28.6 ppm; Anal calcd for C11H14N3O3Cl.0.25 H2O: C, 47.83, H, 5.29; N, 15.21; Cl, 12.84; Found: C, 47.68; H, 5.02; N, 15.23; Cl, 12.92.

المصدر