Thionyl Chloride → 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl chloride

HRID 2306121Notes

Reaction equation

[C:1]1(=[O:15])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12])[C:4](=[O:14])[CH:3]=[CH:2]1.S(Cl)([Cl:18])=O>>[C:1]1(=[O:15])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([Cl:18])=[O:12])[C:4](=[O:14])[CH:3]=[CH:2]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 5736836-Maleimidohexanoic acid

Product 1

HCID 114247166-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl chloride

Procedure

6-Maleimidocaproic acid is treated with excess thionyl chloride at 50° C. for three hours. Remaining thionyl chloride is distilled off to leave the product, 6-maleimidocaproic chloride.

Workup

distillationRemaining thionyl chloride is distilled off

Sources & evidence

ORD record: ord-1bea9609c0264bddae98ddd8a71f4209
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441213B1

Reaction notes

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