Thionyl Chloride → HCID 13427187, compound

HRID 2372370Notes

Reaction equation

C([N:3](C([O-])=O)[N:4]=[C:5]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)C.O=[S:29](Cl)Cl>>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([C:5]2[N:4]=[N:3][S:29][C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 86745573HCID 86745573, compound

Product 1

HCID 13427187HCID 13427187, compoundYield 60.3%

Conditions

Temperature: 50 °C

Procedure

Acylhydrazone 35 (21 g, 58.7 mmol) was added to SOCl2 (80 ml) at 0° C. The temperature was increased to 50° C., and the reaction was complete (by TLC) after 4 hours. SOCl2 was removed under reduced pressure. The crude solid was recrystallized from ETOAc/MeOH to afford 36 (11.6 g, 60.3%) m.p. 185°-186.5° C.

Workup

customafter 4 hours
customSOCl2 was removed under reduced pressure
customThe crude solid was recrystallized from ETOAc/MeOH

Sources & evidence

ORD record: ord-317ddc2401434af4b30d9681bfa3e6ba
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05098918

Reaction notes

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