Réaction #155415

Équation de réaction

3-(methylthio)benzenethiol

sodium metabisulfite

4-fluorobenzaldehyde

→

title compound

Rendement 55.0%

Sodium hydroxy(4-{[3-(methylthio)phenyl]thio}phenyl)methanesulfonate

Rendement 55.0%

Solvants

acetonitrile

acetonitrile

acetonitrile

water

Conditions de réaction

Traitement

1. 1
   Autrewas sparged with nitrogen for 1 hour
2. 2
   Lavagewash)
3. 3
   Lavagewash) and
4. 4
   Températureto cool to ambient temperature
5. 5
   workup.ADDITIONdiluted with ethyl acetate (3 L)
6. 6
   Lavagewashed with hydrochloric acid (2M aqueous solution, 1.5 L) and sodium bicarbonate (1 M aqueous solution, 3 L) and brine (half saturated, 1.5 L)
7. 7
   ConcentrationThe resulting solution was concentrated by distillation at atmospheric pressure to a volume of 2 L
8. 8
   workup.ADDITIONdiluted with acetonitrile (3 L)
9. 9
   Concentrationthe resulting solution was concentrated by distillation at atmospheric pressure to a volume of 2 L
10. 10
    workup.ADDITIONdiluted with acetonitrile (3 L)
11. 11
    Concentrationconcentrated by distillation at atmospheric pressure to a final volume of 3 L
12. 12
    TempératureThe resulting solution was cooled to ambient temperature
13. 13
    Filtrationwas filtered
14. 14
    Autrethe solid collected
15. 15
    Lavagewas washed with water (2-fold 2.5 L) and acetonitrile (2-fold 2.5 L)
16. 16
    workup.STIRRINGstirred at ambient temperature for 18 hours after which time the suspension
17. 17
    Filtrationwas filtered
18. 18
    Lavagethe solid was washed with acetonitrile (2-fold 1 L)
19. 19
    Autredried in vacuo at 50° C.

Mode opératoire

A solution of 3-(methylthio)benzenethiol as prepared in Preparation 8 (290 g, 1.856 mol) in acetonitrile (3 L) was sparged with nitrogen for 1 hour and then treated with 4-fluorobenzaldehyde (196 mL, 1.856 mol) followed by acetonitrile (150 mL, used as a line wash). The resulting solution was treated with 1,1′,3,3′-tetramethylguanidine (256 mL, 2.04 mol) followed by acetonitrile (150 mL used as a line wash) and heated to 50° C. under nitrogen for 16 hours. The resulting solution was allowed to cool to ambient temperature and diluted with ethyl acetate (3 L) and washed with hydrochloric acid (2M aqueous solution, 1.5 L) and sodium bicarbonate (1 M aqueous solution, 3 L) and brine (half saturated, 1.5 L). The resulting solution was concentrated by distillation at atmospheric pressure to a volume of 2 L and diluted with acetonitrile (3 L). the resulting solution was concentrated by distillation at atmospheric pressure to a volume of 2 L and diluted with acetonitrile (3 L) and concentrated by distillation at atmospheric pressure to a final volume of 3 L. The resulting solution was cooled to ambient temperature and treated with a solution of sodium metabisulfite (377 g, 1.982 mol) in water (3 L). After stirring at ambient temperature for 48 hours the resulting suspension was filtered and the solid collected was washed with water (2-fold 2.5 L) and acetonitrile (2-fold 2.5 L). The solid was suspended in acetonitrile (2 L) and stirred at ambient temperature for 18 hours after which time the suspension was filtered and the solid was washed with acetonitrile (2-fold 1 L) and dried in vacuo at 50° C. to give the title compound as a white solid, 55% yield, 368.7 g.

Source