تفاعل #45585

معادلة التفاعل

ammonium acetate

isobutyryl chloride

2-amino-4-fluoro-5-iodo-3-methoxy-6-methylbenzoic acid

pyridine

→

compound

المردود 29.3%

4-Fluoro-3-iodo-6-isobutyrylamino-5-methoxy-2-methylbenzamide

المردود 29.3%

المذيبات

N,N-Dimethylformamide

Ethyl acetate

benzene

Ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   غسيلthe organic layer was washed with 1 N hydrochloric acid (50 ml×2), saturated brine (50 ml)
2. 2
   تجفيفdried over anhydrous magnesium sulfate
3. 3
   تركيزconcentrated under reduced pressure
4. 4
   workup.STIRRINGby stirring at room temperature for 10 minutes
5. 5
   workup.STIRRINGstirring at 50° C. for 45 minutes
6. 6
   غسيلthe organic layer was washed with saturated brine (50 ml×3)
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe residue was purified twice by silica gel column chromatography (chloroform:methanol=100:1→100:7), (n-hexane:ethyl acetate=3:2→chloroform:methanol=50:1)

الإجراء التجريبي

A benzene (10 ml) suspension of 2-amino-4-fluoro-5-iodo-3-methoxy-6-methylbenzoic acid (I-33) (500 mg, 1.54 mmol) was cooled at 0° C., isobutyryl chloride (403 μl, 3.85 mmol), pyridine (311 μl, 3.85 mmol) were put into it, followed by stirring at room temperature for 3 hours. Ethyl acetate (50 ml) was added to the reaction liquid, the organic layer was washed with 1 N hydrochloric acid (50 ml×2), saturated brine (50 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. N,N-Dimethylformamide (5.0 ml), ammonium acetate (593 mg, 7.69 mmol) were added to the residue, followed by stirring at room temperature for 10 minutes, then stirring at 50° C. for 45 minutes. Ethyl acetate (100 ml) was added to the reaction liquid, the organic layer was washed with saturated brine (50 ml×3), dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified twice by silica gel column chromatography (chloroform:methanol=100:1→100:7), (n-hexane:ethyl acetate=3:2→chloroform:methanol=50:1) to obtain the entitled compound (178 mg, 29%) as a colorless solid.

المصدر