Reaktion #472361

Reaktionsgleichung

Carbon disulfide

4-amino-3-methylbenzoic acid

triethylamine

hydrochloric acid

sodium sulfite

iodine

→

4-isothiocyanato-3-methylbenzoic acid

Ausbeute 103.0%

Lösungsmittel

ethyl acetate

water

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe obtained reaction mixture
2. 2
   workup.STIRRINGby stirring at 0° C. for further 1.5 hours
3. 3
   workup.ADDITIONmixed
4. 4
   Sonstigethe organic layer was separated
5. 5
   Einengenconcentrated under reduced pressure to dryness
6. 6
   workup.ADDITIONTo the residue, ethyl acetate (6 mL) and water (1 mL) were added
7. 7
   Waschenthe organic layer was washed once with 1M hydrochloric acid (1 mL)
8. 8
   Einengenconcentrated under reduced pressure to dryness

Vorschrift

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising 4-amino-3-methylbenzoic acid (0.23 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 28 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 1.5 hours. Thereafter, 1M hydrochloric acid (1.5 mL) and sodium sulfite (38 mg, 0.30 mmol) were 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 residue, ethyl acetate (6 mL) and water (1 mL) were added, and the organic layer was washed once with 1M hydrochloric acid (1 mL) and then concentrated under reduced pressure to dryness to obtain 4-isothiocyanato-3-methylbenzoic acid as a cream-colored solid (0.30 g, yield: 103%, HPLC purity: 88%, HPLC retention time: 4.0 min). LC-MS ES-192 (retention time: 4.3 min, condition 1).

Quelle