Dimethyl Sulfoxide → HCID 86613662, compound

HRID 1986046Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[O:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]([CH3:15])([CH3:14])[CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[C:26]([CH2:28]OS(C1C=CC=CC=1)(=O)=O)#[N:27].CS(C)=O>O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[O:5][CH:6]1[CH2:11][C:10]([CH3:12])([CH3:13])[N:9]([CH2:28][C:26]#[N:27])[C:8]([CH3:14])([CH3:15])[CH2:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-(3,4-dichloro-phenoxy)-2,2,6,6-tetramethyl-piperidine (1.22 g, 3.9 mmol), potassium carbonate (6.9 g, 50 mmol), cyanomethylbenzenesulfonate (7.5 ml, 40 mmol) and DMSO (20 ml) was stirred at 70° C. for 15 h. Water (100 ml) was added and the mixture was extracted with diethyl ether (2×50 ml). Chromatography on silica gel with ethyl acetate:petroleum (1:1) gave the title compound. Hydrochloric acid in ether was added and the hydrochloric acid salt was precipitated and stirred for 10 min, followed by filtration. Yield 0.23 g, (16%). Mp >200° C. (Dec.).

Workup

extractionthe mixture was extracted with diethyl ether (2×50 ml)

Sources & evidence

ORD record: ord-549d5685157d48fc9ebd1262392cc8f5
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547788B2

Reaction notes

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