تفاعل #1771285

معادلة التفاعل

7

3,6-Bis(methylcarbamyl)-1,4-dimethoxy-2,5-dinitrobenzene

methanol

hydrochloric acid

→

3,6-Bis(methylcarbamyl)-1,4-dimethoxy-2,5-diaminobenzene

المذيبات

n-butanol acetic acid water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   workup.STIRRINGwith stirring
3. 3
   ترشيحAfter filtering the solution through CELITE
4. 4
   غسيلwashing the filtrate with methanol
5. 5
   أخرىthe solvent was removed in vacuo
6. 6
   أخرىthe residue dried for several hours
7. 7
   أخرىThe dihydrochloride salt of 9 was recrystallized by dissolution in a minimum amount of hot methanol
8. 8
   درجة الحرارةby cooling
9. 9
   workup.ADDITIONaddition of ethyl acetate
10. 10
    أخرى893 mg (88%) yield

الإجراء التجريبي

A mixture consisting of 978 mg (2.84 mmol) of 7, 100 mg 5% Pd/C, and 100 mL of methanol was shaken under 50 psi of H2 for 4 hours. Upon completing the reduction, 10 mL of concentrated hydrochloric acid was added to the reaction mixture with stirring. After filtering the solution through CELITE and washing the filtrate with methanol, the solvent was removed in vacuo and the residue dried for several hours. The dihydrochloride salt of 9 was recrystallized by dissolution in a minimum amount of hot methanol followed by cooling and then addition of ethyl acetate: 893 mg (88%) yield; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.44; 1H NMR (dimethyl-d6 sulfoxide) δ8.40 (2H, brs, 3- and 6-carbamyl proton), 3.64 (6H, s, methoxys), 2.81 (6H, d, J=4.0 Hz, 3- and 6-carbamyl methyls); mass spectrum (EI mode), m/z 282 (P+).

المصدر