反応 #2358596

反応方程式

oxalyl chloride

dimethylformamide

TEA

aniline

ethyl acetate hexane

ethyl acetate hexane

→

required product

2-(4-(phenylcarbamoyl)phenyl)propanoic acid

溶媒

dichloromethane

dichloromethane

dichloromethane

water

反応条件

後処理

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   その他Reaction contents
3. 3
   その他As the reaction not
4. 4
   その他reaction contents
5. 5
   温度were heated to 40° C.
6. 6
   workup.STIRRINGstirred for 1 hr at the same temperature
7. 7
   workup.DISTILLATIONDichloromethane was distilled off completely under reduced pressure
8. 8
   workup.STIRRINGstirred the contents for 15 minutes at 0° C
9. 9
   workup.ADDITIONadded dropwise at 0° C.
10. 10
    workup.STIRRINGto stir for 1 hr at 0° C
11. 11
    workup.ADDITIONwas added
12. 12
    その他the layers formed
13. 13
    その他were separated out
14. 14
    乾燥Organic layer was dried over sodium sulfate
15. 15
    濃縮concentrated under reduced pressure

実験手順

Step f-g: To a stirred solution of step-e product (2.3 g, 10 mmol) in dichloromethane (23 ml), oxalyl chloride (2.08 g (1.44 ml), 16 mmol, 1.5 eq) followed by catalytic amount of dimethylformamide were added at room temperature. Reaction contents were stirred for 20 minutes at room temperature. Progress of the reaction was monitored by TLC (5% ethyl acetate-hexane, Rf˜0.7). As the reaction not moved completely, reaction contents were heated to 40° C. and stirred for 1 hr at the same temperature. Again TLC was checked and confirmed that the starting material was disappeared. Dichloromethane was distilled off completely under reduced pressure. In another round-bottom flask, TEA (triethylamine) (3.2 g (2.5 ml), 25 mmol, 2.5 eq) was added to a solution of aniline (0.83 g, 9 mmol) in dichloromethane (10 ml) and stirred the contents for 15 minutes at 0° C. Then the above prepared acid chloride was taken in dichloromethane (13 ml) and added dropwise at 0° C. and the overall reaction mixture was allowed to stir for 1 hr at 0° C. Progress of the reaction was monitored by TLC (5% ethyl acetate-hexane, Rf˜0.3). On completion of the reaction, water (10 ml) was added and the layers formed were separated out. Organic layer was dried over sodium sulfate and concentrated under reduced pressure to yield the required product as an off white solid (3 g, 96%).

出典