Thionyl Chloride → HCID 131730570, compound

HRID 1892542Notes

Reaction equation

[C:1]([C:3]([S:13][CH2:14][CH3:15])=[CH:4][C@@H:5]1[C@@H:7]([C:8](O)=[O:9])[C:6]1([CH3:12])[CH3:11])#[N:2].S(Cl)([Cl:18])=O>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([C:3]([S:13][CH2:14][CH3:15])=[CH:4][C@@H:5]1[C@@H:7]([C:8]([Cl:18])=[O:9])[C:6]1([CH3:12])[CH3:11])#[N:2]

Participants

Conditions

Temperature: 65 °C

Procedure

To methyl=(1R)-trans-3-[(1EZ)-2-cyano-2-(ethylthio)ethenyl]-2,2-dimethylcyclopropanecarboxylic acid (8.98 g, 39.9 mmol), toluene (25 mL) was added and then thionyl chloride (5.0 g, 42.0 mmol) was added. Furthermore, N,N-dimethylformamide (50 mg) was added, followed by stirring at an inner temperature of 60 to 70° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to obtain 9.62 g of (1R)-trans-3-[(1EZ)-2-cyano-2-(ethylthio)ethenyl]-2,2-dimethylcyclopropanecarboxylic acid chloride represented by the following formula:

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-838a6fb251a34367b42bef68a92e1523
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507692B2

Reaction notes

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