Thionyl Chloride → HCID 86616222, compound

HRID 502945Notes

Reaction equation

S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[C:12]1([C:17]([OH:19])=O)[CH2:16][CH2:15][CH2:14][CH2:13]1>CN(C=O)C>[Cl:5][C:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[C:12]1([C:17]([Cl:3])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Conditions

Temperature: 75 °C

Procedure

DMF (a catalytic amount) was added to a thionyl chloride (15 ml) solution of 1-(3-chloro-4-methyl-2-thienyl)cyclopentanecarboxylic acid (1.59 g), followed by stirring at 75° C. for 30 minutes. The reaction solution was subjected to evaporation under reduced pressure to obtain 1-(3-chloro-4-methyl-2-thienyl)cyclopentanecarbonyl chloride. A THF (20 ml) solution of 1-(3-chloro-4-methyl-2-thienyl)cyclopentanecarbonyl chloride was added dropwise to a THF (20 ml) solution of hydrazine monohydrate (12.6 ml) at 0° C., followed by stirring at 0° C. for 3 hours. After the reaction solution and chloroform were added to a saturated aqueous sodium hydrogen carbonate solution, the organic layer was separated. The organic layer washed with brine and, after drying over anhydrous sodium sulfate and filtration, the solvent was removed by evaporation under reduced pressure to obtain 1.65 g of 1-(3-chloro-4-methyl-2-thienyl)cyclopentanecarbohydrazide (pale yellow solid).

Workup

customThe reaction solution was subjected to evaporation under reduced pressure

Sources & evidence

ORD record: ord-01b143d5665f48a1b169acbe962adf83
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776897B2

Reaction notes

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