反応 #972

反応方程式

(-)-S-Methyl-L-cysteine

triethylamine

2,4-difluoronitrobenzene

→

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

溶媒

water

acetone

反応条件

後処理

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
   その他the acetone is then stripped off under reduced pressure on a rotary evaporator
5. 5
   その他the aqueous residue is transferred to a separating funnel
6. 6
   抽出extracted 2× with approximately 50 ml of methyl tert-butyl ether (MTB ether)
7. 7
   その他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
    その他are formed
12. 12
    その他The ether phase is separated off
13. 13
    抽出the aqueous phase is extracted once again with 50 ml of MTB ether
14. 14
    乾燥The extracts are dried over sodium sulfate
15. 15
    その他evaporated on a rotary evaporator

実験手順

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).

出典