反应 #972

反应方程式

(-)-S-Methyl-L-cysteine

triethylamine

2,4-difluoronitrobenzene

→

N-(5-Fluoro-2-nitrophenyl)-S-methyl-L-cysteine

溶剂

water

acetone

反应条件

后处理

1. 1
   温度The mixture is heated
2. 2
   温度to reflux for 7.5 hours
3. 3
   workup.STIRRINGwhile stirring (orange-colored solution)
4. 4
   其他the acetone is then stripped off under reduced pressure on a rotary evaporator
5. 5
   其他the aqueous residue is transferred to a separating funnel
6. 6
   萃取extracted 2× with approximately 50 ml of methyl tert-butyl ether (MTB ether)
7. 7
   其他The aqueous phase is transferred to a four-necked flask
8. 8
   workup.ADDITION150 ml of MTB ether are added to it
9. 9
   温度while being cooled (<25° C.)
10. 10
    workup.STIRRINGThe mixture is then stirred thoroughly until clear phases
11. 11
    其他are formed
12. 12
    其他The ether phase is separated off
13. 13
    萃取the aqueous phase is extracted once again with 50 ml of MTB ether
14. 14
    干燥The extracts are dried over sodium sulfate
15. 15
    其他evaporated on a rotary evaporator

实验过程

16.2 g of (-)-S-Methyl-L-cysteine (0.1 mol) are suspended in a mixture of 120 ml of water and 120 ml of acetone in a four-necked flask under N2. 30.4 ml (22.2 g) of triethylamine (0.22 mol) are added rapidly while stirring. 15.9 g of 2,4-difluoronitrobenzene (0.1 mol) are added, with further stirring, to the resulting yellow solution. The mixture is heated to reflux for 7.5 hours while stirring (orange-colored solution) and the acetone is then stripped off under reduced pressure on a rotary evaporator; the aqueous residue is transferred to a separating funnel and extracted 2× with approximately 50 ml of methyl tert-butyl ether (MTB ether). This extract is composed, in the main, of 2,4-difluoronitrobenzene and is discarded. The aqueous phase is transferred to a four-necked flask and 150 ml of MTB ether are added to it, after which the mixture is adjusted, while being cooled (<25° C.), to pH 1 with approximately 25 ml of 38% sulfuric acid. The mixture is then stirred thoroughly until clear phases are formed. The ether phase is separated off and the aqueous phase is extracted once again with 50 ml of MTB ether. The extracts are dried over sodium sulfate and evaporated on a rotary evaporator. The yield comprises 27 g of a yellow oil which soon solidifies. M.p. 147° (from water/methanol).

来源