تفاعل #9208

معادلة التفاعل

methanol

1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea

1-(6-Bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea

potassium carbonate

benzyl bromide

→

desired compound 9

المردود 45.0%

1-(6-Bromo-7-benzyloxy-2-benzothiazolyl)-3-ethyl-urea

المردود 45.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas cooled down to about 0° C
2. 2
   workup.STIRRINGwas stirred at about 0° C. for about 16 hours
3. 3
   ترشيحThe solid was filtered off
4. 4
   غسيلrinsed with methanol (3 mL)
5. 5
   أخرىThe solvent was evaporated
6. 6
   workup.DISSOLUTIONthe residue was dissolved in DMF (2 mL)
7. 7
   أخرىThe crude reaction solution
8. 8
   أخرىwas purified by LC/MS

الإجراء التجريبي

A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6 (0.050 g, 0.16 mmol) and potassium carbonate (0.023 g, 0.17 mmol, 1.05 eq) in anhydrous DMF (1.6 mL) was stirred at about 20° C. for about 0.5 hour, and was cooled down to about 0° C. The reaction mixture was treated with benzyl bromide (0.019 mL, 0.16 mmol, 1.0 eq), and was stirred at about 0° C. for about 16 hours. To the reaction mixture was added methanol (10 mL). The solid was filtered off and rinsed with methanol (3 mL). The solvent was evaporated and the residue was dissolved in DMF (2 mL). The crude reaction solution was purified by LC/MS to give 0.029 g (45%) of the desired compound 9. 1H NMR (DMSO) δ 10.86 (br s, 1H, NH), 7.59–7.34 (m, 7H, ArH), 6.72 (br s, 1H, NH), 5.17 (s, 2H, CH2), 3.18 (m, 2H, CH2), 1.09 (t, 3H, J=7.2 Hz, CH3); LC/MS 406 (MH+); RP-HPLC RT 3.8 minutes.

المصدر