反应 #472372

反应方程式

iodine

Carbon disulfide

trans-4-(aminomethyl)cyclohexanecarboxylic acid

triethylamine

hydrochloric acid

→

trans-4-(isothiocyanatomethyl)cyclohexanecarboxylic acid

收率 101.0%

溶剂

tetrahydrofuran

water

tetrahydrofuran

ethyl acetate

反应条件

后处理

1. 1
   其他The obtained reaction mixture
2. 2
   workup.STIRRINGby stirring at 0° C. for further two hours
3. 3
   workup.ADDITIONmixed
4. 4
   其他the organic layer was separated
5. 5
   浓缩concentrated under reduced pressure to dryness
6. 6
   workup.ADDITIONTo the obtained residue, a solvent mixture of hexane (3 mL) and ethyl acetate (3 mL)
7. 7
   workup.ADDITIONwas added
8. 8
   workup.ADDITIONthoroughly mixed
9. 9
   过滤the insoluble matter was filtered off
10. 10
    浓缩Then, the filtrate was concentrated under reduced pressure to dryness

实验过程

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising trans-4-(aminomethyl)cyclohexanecarboxylic acid (0.24 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0 mL) and triethylamine (0.51 mL, 3.6 mmol), followed by stirring at room temperature for 44 hours. The obtained reaction mixture was dropwise added to a tetrahydrofuran (1.0 mL) solution of iodine (0.41 g, 1.6 mmol) over a period of 5 minutes at 0° C., followed by stirring at 0° C. for further two hours. Thereafter, 1M hydrochloric acid (1.5 mL) was added and mixed. Then, ethyl acetate (6 mL) was added, and the organic layer was separated and concentrated under reduced pressure to dryness. To the obtained residue, a solvent mixture of hexane (3 mL) and ethyl acetate (3 mL) was added and thoroughly mixed, and the insoluble matter was filtered off. Then, the filtrate was concentrated under reduced pressure to dryness to obtain trans-4-(isothiocyanatomethyl)cyclohexanecarboxylic acid as a ocher solid (0.30 g, yield: 101%, and 1H-NMR spectrum showed no distinct by-product). LC-MS ES-198(retention time: 20.3 min, condition 3).

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