Methyl iodide → Benzene, 1,2,4,5-tetrakis(methylthio)-

Temperature

10 °C

Into a 3-neck 1 liter flask equipped with a thermometer, magnetic stirring bar, and gas inlet and outlet tubes was placed a solution of 25 g (66.72 millimoles) of the product of Example 1 in 300 ml of dry pyridine. The mixture was heated rapidly to 105°-110° C. and 8.29 g of Na pellets (360 millimoles) were added rapidly against a nitrogen flow. The reaction mixture was maintained below reflux but above 100° C. for 1 hour until all of the sodium had reacted. The mixture was then cooled to 10° C. and methyl iodide (24 ml) was added slowly by means of a syringe. The resulting mixture was stirred for 40 minutes and quenched with 350 ml of saturated aqueous NaCl. Water was then added to form a dilute suspension which was filtered under suction and washed copiously with water to yield a yellow, crystalline solid. The solid was washed with 150 ml of -10° C. methanol to yield 11.5 g (66%) of white product; mp:127°-129° C.

1. customInto a 3-neck 1 liter flask equipped with a thermometer, magnetic stirring bar, and gas inlet and outlet tubes
2. temperatureThe mixture was heated rapidly to 105°-110° C.
3. temperatureThe reaction mixture was maintained
4. customhad reacted
5. customquenched with 350 ml of saturated aqueous NaCl
6. additionWater was then added
7. customto form a dilute suspension which
8. filtrationwas filtered under suction
9. washwashed copiously with water
10. customto yield a yellow, crystalline solid
11. washThe solid was washed with 150 ml of -10° C. methanol

ORD record

ord-33e20e193fb34282a91a99a60e175282

Source dataset

uspto-grants-1986_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04626586