Isoamyl Nitrite → Ethyl [(4-chloro-2-{[2-chloro-4-(ethylsulfonyl)phenyl]thio}phenyl)thio]acetate

HRID 910836Notes

Reaction equation

[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(ON=O)CC(C)C.[Cl:16][C:17]1[CH:23]=[CH:22][C:20](N)=[C:19]([S:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH2:34][CH3:35])(=[O:33])=[O:32])=[CH:27][C:26]=2[Cl:36])[CH:18]=1>C(#N)C.O>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:19]([S:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH2:34][CH3:35])(=[O:32])=[O:33])=[CH:27][C:26]=2[Cl:36])[CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl mercaptoacetate (0.11 ml) followed by isoamylnitrite (0.16 ml) were added to a solution of the product from step (iii) (0.35 g) in dry acetonitrile (20 ml) and heated at 60° C. for 10 h. The mixture was diluted with water, extracted with diethylether, the organics dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with isohexane/diethylether 1:1, yield 0.10 g.

Workup

extractionextracted with diethylether
customthe organics dried
customevaporated under reduced pressure
customThe residue was purified by chromatography on silica eluting with isohexane/diethylether 1:1, yield 0.10 g

Sources & evidence

ORD record: ord-ec67782cf61649b6a1a16fef9e985863
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022248B2

Reaction notes

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