تفاعل #47011

معادلة التفاعل

intermediate 59

cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic acid, tert-butyl ester

4-fluorobenzylamine

→

product 85

المردود 41.6%

2-(4-Fluorobenzylamino)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester

المردود 41.6%

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture is cooled to RT
2. 2
   أخرىpartitioned between dichloromethane and water
3. 3
   أخرىThe organic solution is separated
4. 4
   تجفيفdried (MgSO4)
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue is purified by chromatography on silica gel
7. 7
   غسيلgradient elution with heptane:EtOAc (80:20-40:60)

الإجراء التجريبي

A mixture of intermediate 59 (1.0 g, 0.0027 mol), 4-fluorobenzylamine (0.372 mL, 0.00321 mol) and MeOH (0.4 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and partitioned between dichloromethane and water. The organic solution is separated, dried (MgSO4), and concentrated in vacuo. The residue is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (80:20-40:60) gives 0.50 g of the product 85. 1H NMR (CDCl3) δ 7.60-7.35 (m, 3 H), 7.15-6.90 (m, 10 H), 6.85-6.70 (m, 2 H), 5.50-5.30 (m, 2 H), 5.75-5.55 (m, 2 H), 1.12 (s, 9 H); MS: m/z 446 (M++1).

المصدر