Thionyl Chloride → HCID 58136651, compound

HRID 877162Notes

Reaction equation

[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7](O)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:32])=O>>[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7]([Cl:32])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24386Thionyl Chloride2×

HCID 58074507cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid

Product 1

HCID 58136651HCID 58136651, compound

Conditions

Temperature: 50 °C

Procedure

At room temperature, 8.9 g (22.68 mmol) of rac-cyclopentyl{-4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid were stirred with 63.6 ml (871.5 mmol) of thionyl chloride for 2 h. The reaction solution was then warmed to 50° C. and stirred for a further 2 h. After the reaction had gone to completion, the reaction solution was freed from the thionyl chloride under reduced pressure. This gave 7.7 g (18.74 mmol, 82% of theory) of the title compound as a colorless oil, which was used without further purification in subsequent reactions.

Workup

customThis gave 7.7 g (18.74 mmol, 82% of theory) of the title compound as a colorless oil, which was used without further purification in subsequent reactions

Sources & evidence

ORD record: ord-dbf855f864a84921bd56dd76148d2bcf
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987256B2

Reaction notes

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