2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile Chemical Properties

Melting point:

67-69°C

Boiling point:

360.8±52.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

-8.49±0.20(Predicted)

form 

Solid

color 

Off-White to Light Yellow

InChI

InChI=1S/C7H10N2O2S/c1-2-12(10,11)9-5-7(6-9)3-4-8/h3H,2,5-6H2,1H3

InChIKey

HQUIOHSYUKWGOM-UHFFFAOYSA-N

SMILES

C(#N)/C=C1\CN(S(CC)(=O)=O)C\1

Safety Information

HS Code 

2933998090

2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile Usage And Synthesis

Uses

2-(1-(Ethylsulfonyl)azetidin-3-ylidene)acetonitrile is an intermediate in the synthesis of Baricitinib, a JAK 1 and 2 inhibitor used in the treatment of rheumatoid arthritis.

Synthesis

2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile is synthesized by first treating azetidine-3-ol hydrochloride with an equimolar equivalent of an alkanesulfonyl chloride, preferably ethanesulfonyl chloride, to give l-ethylsulfonylazetidin-3-ol. Preferably, the reaction is performed in a biphasic solution comprising a mixture of an organic phase and a aqueous phase, preferably THF with an aqueous solution which is basic, while maintaining the solution at room temperature or a temperature slightly below room temperature, preferably 20 °C. The reaction is followed to completion using standard monitoring techniques. Typically, the reaction is complete within 1 to 5 hours. The organic layer is removed, preferably by distillation, and the aqueous layer is extracted with an appropriate solvent such as toluene, p-cymene, and CPME. Preferably the extraction solvent is toluene. Alternatively, the toluene extractions can be excluded if recrystallization of 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile is performed.

2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile(1187595-85-2)Related Product Information

• Baricitinib
• 4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
• 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• 4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine