Ethanethiol → 2-Ethylthio-3-nitropyrrole

Temperature

175 °C

Using a microwave chemical reactor (CEM Explorer Microwave System manufactured by CEM Corporation, 3100 Smith Farm Road, Matthews N.C., 28106-0200), 0.1 gram (0.70 millimole) of 2-chloro-3-nitropyrrole (prepared in Steps D-F of Example 1), 0.5 mL (excess) of ethylmercaptan and 0.2 mL of ethyldiisopropylamine (excess) in 5 mL of acetonitrile were placed in an appropriate 10 mL vile. The vile was sealed and placed in the reaction chamber of the microwave chemical reactor. At 150 watts of power, the microwave reactor was brought to 100° C. during a five-minute period, where it was maintained for a 30-minute period. In a like manner the reactor was brought to 150° C. where it was maintained for a 30-minute period, and finally to 175° C. where it was maintained for a 30-minute period, after which time the reaction was considered to be complete. Upon completion of the reaction the microwave reactor was cooled, and the vile containing the reaction mixture was removed from the reactor and absorbed onto silica gel. The silica gel-reaction mixture combination was then subjected to column chromatography. Elution was accomplished using 33% diethyl ether in hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.03 gram of the subject compound. The NMR spectrum was consistent with the proposed structure. The reaction was repeated.

1. customThe vile was sealed
2. customwas brought to 100° C. during a five-minute period, where it
3. temperaturewas maintained for a 30-minute period
4. customwas brought to 150° C.
5. temperaturewas maintained for a 30-minute period
6. customUpon completion of the reaction the microwave reactor
7. temperaturewas cooled
8. additionthe vile containing the reaction mixture
9. customwas removed from the reactor
10. customabsorbed onto silica gel
11. customThe silica gel-reaction mixture combination
12. washElution
13. concentrationconcentrated under reduced pressure

ORD record

ord-69261220f6434b7eb8180957e458240b

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943642B2