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ChemicalBook CAS DataBase List p-Toluenesulfonyl Isocyanate
4083-64-1

p-Toluenesulfonyl Isocyanate synthesis

14synthesis methods
Add the organic azide (0.75 mmol), Pd(OAc)2 (5.6 mg, 5 mol%) to an oven-dried Schlenk tube (10 mL). Purge the tube and backfill with CO (three cycles) from a balloon. Inject anhydrous MeCN (3.0 mL) into the tube. Stir at 80°C for 4 h under CO atmosphere (balloon). Concentrate the mixture under reduced pressure. Purify the residue by column chromatography (petroleum ether/EtOAc 3:1.-.1:1).

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Yield:4083-64-1 98.33%

Reaction Conditions:

in chlorobenzene at 90 - 105; for 4 h;Temperature;

Steps:

1-6

p-toluenesulfonamide 86.04g (content 99.5%, 0.5mol, p-toluenesulfonamide:Dimethyl carbonate = 1:1.1) and 86 g of chlorobenzene were stirred to dissolve, and added to a constant pressure dropping funnel.After the chlorination reaction is completed, the p-toluenesulfonamide chlorobenzene solution is added to the four-necked flask,The temperature was raised to above 90 °C with stirring, and the temperature was controlled at 105 °C for 4 hours.Sampling to detect the complete reaction of the raw materials, connect the condenser tube and the receiving bottle, start to recover the solvent chlorobenzene, control the vacuum degree to -0.08Mpa and the recovery temperature to 105°C.After the solvent chlorobenzene recovery is completed, the material is transferred into the distillation flask,Connect the vacuum pump to evacuate to below -0.095Mpa, heat up and distill,97.73 g of p-toluenesulfonyl isocyanate were obtained, the detected content was 99.19%, and the experimental yield was 98.33%.

References:

CN114181120,2022,A Location in patent:Paragraph 0007; 0015-0038

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