تفاعل #440189

معادلة التفاعل

2-methylbenzimidazole

4-chloromethylstyrene

potassium hydroxide

potassium carbonate

→

1-(4-vinylbenzyl)-2-methylbenzimidazole

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىthe synthesis
2. 2
   ترشيحThe reaction mixture was filtered
3. 3
   استخلاصthe solid residue extracted with additional tetrahydrofuran
4. 4
   تركيزThe combined liquids were concentrated at reduced pressure
5. 5
   أخرىthe resulting brown oil was triturated with ligroin
6. 6
   workup.WAITheld at −15° C. for a few hours
7. 7
   أخرىcrystallization
8. 8
   أخرىThe ligroin was decanted from the product, which
9. 9
   أخرىwas then purified by recrystallization from 70% methanol/30% water
10. 10
    أخرىwas obtained
11. 11
    أخرىafter drying

الإجراء التجريبي

This Example illustrates the synthesis of polymeric blocked developer PBD1. First, 1-(4-vinylbenzyl)-2-methylbenzimidazole was prepared. A suspension of 2-methylbenzimidazole (25.0 g, 0.19 mol), 4-chloromethylstyrene (31.8 g, 0.21 mol), powdered potassium hydroxide (10.6 g, 0.19 mol), and potassium carbonate (13.1 g, 0.1 mol) in 200 mL of dry tetrahydrofuran was stirred at 25° C. for 5 d. The reaction mixture was filtered, and the solid residue extracted with additional tetrahydrofuran. The combined liquids were concentrated at reduced pressure, and the resulting brown oil was triturated with ligroin and held at −15° C. for a few hours to induce crystallization. The ligroin was decanted from the product, which was then purified by recrystallization from 70% methanol/30% water. A cream colored solid product (43.2 g, 92%) was obtained after drying. 1H NMR (CDCl3) δ 2.61 (s, 3H), 5.28 (d, J=11.0, 1H), 5.33 (s, 2H), 5.75 (d, J=17.6, 1H), 6.7 (m, 1H), 7.05 (d, J=8.1, 2H), 7.25 (m, 2H), 7.37 (d, J=8.2, 2H), 7.78 (d, J=7.3, 1H). Electrospray mass spectrometry (ES-MS) m/e 249+ (M+1).

المصدر