Реакция #155415

Уравнение реакции

3-(methylthio)benzenethiol

sodium metabisulfite

4-fluorobenzaldehyde

→

title compound

Выход 55.0%

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

Выход 55.0%

Растворители

acetonitrile

acetonitrile

acetonitrile

water

Условия реакции

Обработка

1. 1
   Другоеwas sparged with nitrogen for 1 hour
2. 2
   Промывкаwash)
3. 3
   Промывкаwash) and
4. 4
   Температураto cool to ambient temperature
5. 5
   workup.ADDITIONdiluted with ethyl acetate (3 L)
6. 6
   Промывкаwashed 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
   КонцентрированиеThe 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
   Концентрированиеthe 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
    Концентрированиеconcentrated by distillation at atmospheric pressure to a final volume of 3 L
12. 12
    ТемператураThe resulting solution was cooled to ambient temperature
13. 13
    Фильтрацияwas filtered
14. 14
    Другоеthe solid collected
15. 15
    Промывкаwas 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
    Фильтрацияwas filtered
18. 18
    Промывкаthe solid was washed with acetonitrile (2-fold 1 L)
19. 19
    Другоеdried in vacuo at 50° C.

Методика

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.

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