تفاعل #590085

معادلة التفاعل

1,1′-carbonyldiimidazole

THF

(5-fluoro-2-nitrophenyl)isopropylamine

→

title compound

المردود 63.8%

6-fluoro-1-isopropyl-1,3-dihydro-2H-benzimidazol-2-one

المردود 63.8%

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe catalyst was filtered off on a pad of Celite
2. 2
   أخرىthe filtrate was evaporated under reduced pressure
3. 3
   workup.STIRRINGstirred at 100° C. for 10 h
4. 4
   درجة الحرارةAfter cooling
5. 5
   أخرىthe volatile materials were removed under reduced pressure
6. 6
   أخرىthe residue was partitioned between ethylacetate and H2O
7. 7
   استخلاصAfter extraction with ethylacetate (3 times)
8. 8
   غسيلthe combined organic phase was washed with brine
9. 9
   تجفيفdried over MgSO4
10. 10
    تركيزconcentrated
11. 11
    أخرىThe residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (2:1)

الإجراء التجريبي

A mixture of (5-fluoro-2-nitrophenyl)isopropylamine (Step 1 of Example 9, 5.85 g, 30 mmol) and 10% Pd—C (600 mg) in MeOH was stirred under atmosphere of hydrogen gas at room temperature for 12 h. The catalyst was filtered off on a pad of Celite, and the filtrate was evaporated under reduced pressure. To the residue was added 1,1′-carbonyldiimidazole (4.5 g, 28 mmol) and THF (100 μL) and then stirred at 100° C. for 10 h. After cooling, the volatile materials were removed under reduced pressure and the residue was partitioned between ethylacetate and H2O. After extraction with ethylacetate (3 times), the combined organic phase was washed with brine, dried over MgSO4 and concentrated. The residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (2:1) to give 3.47 g (60%) of the title compound as a white solid.

المصدر