Reaktion #42440

Reaktionsgleichung

sodium acetate

3-amino-4-methyl benzoic acid

hydrochloric acid

2-methyl-2-propanethiol

Sodium nitrite

→

title compound

3-[(E)-(Tert-butylthio)diazenyl]-4-methylbenzoic acid

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONslowly added to the mixture at 0° C
2. 2
   workup.ADDITIONwas added
3. 3
   Filtrationthe resulting solids were collected by filtration
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried under reduced pressure

Vorschrift

To a mixture of 3-amino-4-methyl benzoic acid (5.0 g) in water (50 mL) was added concentrated hydrochloric acid (15 mL). The mixture was chilled to 0° C. in an ice/acetone bath. Sodium nitrite (2.28 g) was dissolved in water (10 mL) and slowly added to the mixture at 0° C. The pH was adjusted to 6 with saturated sodium acetate and 2-methyl-2-propanethiol (1.8 mL) was added. The mixture was stirred for 1 h and the resulting solids were collected by filtration, washed with water and dried under reduced pressure to give 5.7 g of the title compound: 1H NMR (CDCl3) δ 1.61, 2.20, 7.38, 7.55, 9.67.

Quelle