Pyridine → N,N-diethyl-1-methyl-2-(2-(2-methyl-2-(phenylcarbonothioyl)hydrazinyl)-2-oxoethylsulfanyl)hydrazinecarbothioamide

44 mg (0.25 mmol) 2-(chlorosulfonyl)acetyl chloride dissolved in 1 ml dry THF was treated with 42 mg (0.25 mmol) N-methylbenzothiohydrazide dissolved in 0.5 ml THF at 0° C. over 15 min. The reaction was stirred for 15 min and then checked by TLC if the thiohydrazide has completely reacted. Now 40 mg (0.25 mmol) N,N-diethyl-1-methylhydrazinecarbothioamide dissolved in 0.5 ml THF was added and the mixture stirred at 0° C. for 15 min. Then 60 μl (0.75 mmol) pyridine was added and the reaction allowed to warm up to r.t. overnight. The reaction was quenched with 5 ml water, the pH adjusted to 11 and extracted with 5 ml ethyl acetate. The pH was reduced to 4-5 and the aqueous phase extracted 2 times with 5 ml ethyl acetate. The latter extracts were dried over MgSO4 and concentrated. If the purity was not satisfactory (<90%) it was purified on silica with DCM/MeOH (5-20%)/NH4OH (1%). ESMS (C16H25N5O3S3): calc'd. 431.11. Found: 432.2 [M+H+].

1. customhas completely reacted
2. additionwas added
3. stirringthe mixture stirred at 0° C. for 15 min
4. customThe reaction was quenched with 5 ml water
5. extractionextracted with 5 ml ethyl acetate
6. extractionthe aqueous phase extracted 2 times with 5 ml ethyl acetate
7. dry with materialThe latter extracts were dried over MgSO4
8. concentrationconcentrated
9. customwas purified on silica with DCM/MeOH (5-20%)/NH4OH (1%)

ORDレコード

ord-839173589abb44b19b4dc86531afe3a9

出典データセット

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08680100B2