反応 #80928

反応方程式

acetic anhydride

acetic anhydride

acetyl nitrate

nitric acid

acetyl nitrate

2-methylaniline

4-fluoro-2-methylaniline

→

5-fluoro-2-methylcarbonylamino-3-methylnitrobenzene

反応条件

後処理

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   workup.STIRRINGof stirred
3. 3
   その他placed in a dropping funnel
4. 4
   workup.ADDITIONUpon completion of addition
5. 5
   workup.STIRRINGthe reaction mixture was stirred an additional 5 hours
6. 6
   ろ過The resultant solid was collected by filtration
7. 7
   洗浄washed with water
8. 8
   その他dried at 60° C. under vacuum

実験手順

Stirred acetic anhydride, 300 mL, was cooled to about 7° C., and 25.1 grams (0.20 mole) of 4-fluoro-2-methylaniline was added dropwise during a 30 minute period. Upon completion of addition, the reaction mixture was stirred at about 10° C. for an additional 15 minutes. In a separate reaction vessel, acetyl nitrate was prepared by the dropwise addition of 14.9 mL of 90% nitric acid to 30 mL of stirred, cold (0°-15° C.) acetic anhydride during a 15 minute period. The so-prepared acetyl nitrate was cooled to about -5° C., placed in a dropping funnel, and added dropwise during a 30 minute period to the 2-methylaniline solution. Upon completion of addition, the reaction mixture was stirred an additional 5 hours. After this time the reaction mixture was poured into 400 grams of ice. The resultant solid was collected by filtration, washed with water, and dried at 60° C. under vacuum, yielding 23.0 grams of 5-fluoro-2-methylcarbonylamino-3-methylnitrobenzene, mp 167°-172° C. The NMR spectrum was consistent with the proposed structure.

出典