ChemicalBook CAS DataBase List 1-(Acetylthiomethyl)cyclopropaneacetonitrile

1-(Acetylthiomethyl)cyclopropaneacetonitrile synthesis

6synthesis methods

Product Name:1-(Acetylthiomethyl)cyclopropaneacetonitrile
CAS Number:152922-72-0
Molecular formula:C8H11NOS
Molecular Weight:169.24

1-(Hydroxymethyl)cyclopropaneacetonitrile

152922-71-9
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507-09-5
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1-(Acetylthiomethyl)cyclopropaneacetonitrile

152922-72-0
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Yield:152922-72-0 93%

Reaction Conditions:

with triethylamine in ethanol;water;N,N-dimethyl-formamide;toluene;

Steps:

3.B Method B.

Method B. A solution of 1-(hydroxymethyl)cyclopropaneacetonitrile (34.2 g, 0.308 mol) in toluene:DMF (1.9:1,210 mL) and triethylamine (49.4 mL, 0.354 mol) were combined in a 3-neck, 1L round bottom flask equipped with mechanical stirring and a thermocouple, flushed with nitrogen and cooled to -15° C. Mesyl chloride (26 mL) was added dropwise over 0.5 hr., keeping the temperature below 5° C. Ethanol (77 mL), triethylamine (86 mL, 0.616 mol) and thiolacetic acid (26.4 mL) were added sequentially as quickly as possible. The mixture was removed from the cooling bath and heated to 35° C. This temperature was maintained until <1% mesylate remains, about 7 hrs. Water (250 mL) was added and the mixture was shaken. The phases were separated, the aqueous phase was back-extracted with toluene (200 mL), and the organic phases were combined to provide the title compound (48.3 g at 103 mg/mL, 93% yield, purity: 91 area %).

References:

US5614632,1997,A