Thionyl Chloride → 4-[chloro(8-quinolinyl)methyl]-N,N-diethylbenzamide

HRID 1837544Notes

Reaction equation

[CH2:1]([N:3]([CH2:24][CH3:25])[C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)=[CH:7][CH:6]=1)[CH3:2].O=S(Cl)[Cl:28]>C(Cl)Cl>[Cl:28][CH:11]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)[C:8]1[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH2:24][CH3:25])[CH2:1][CH3:2])=[O:23])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Compound II (2.0 g, 6.6 mmol) was dissolved in dry CH2Cl2 (25 mL) and SOCl2 (0.53 mL, 7.3 mmol) was added. The solution was stirred at 25° C. for 30 min and the solvent was evaporated in vacuo. Compound III was obtained as an oil (˜100%) and used in the next reaction without further purification.

Workup

customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-5f23844e816b40e9b87f1363ec549fcb
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06784181B2

Reaction notes

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