Hydrochloric Acid → HCID 178527472, compound

HRID 631867Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

N-(2-Cyano-3-cyclopropylphenyl)-benzenesulfonamide (Intermediate 9, 0.052 g), azidotrimethyl-silane (0.087 g) and dibutyltin oxide (0.038 g) were suspended in 1,2-dichloroethane (3 mL). The mixture was heated by microwave irradiation at 140° C. for 45 minutes. Six further aliquots of azidotrimethylsilane (0.174 g) were added and after each addition the mixture was heated by microwave irradiation at 140° C. for 60 minutes. The reaction mixture was acidified to pH 1 using 1N hydrochloric acid, and then extracted with ethyl acetate. The combined organic extracts were dried with magnesium sulfate, filtered and the filtrate was evaporated under vacuum. The residue was triturated with a mixture of pentane and cyclohexane and the solid was collected by filtration, to give the title compound as a white solid (0.039 g).

Workup

additionafter each addition the mixture
temperaturewas heated by microwave irradiation at 140° C. for 60 minutes
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts were dried with magnesium sulfate
filtrationfiltered
customthe filtrate was evaporated under vacuum
customThe residue was triturated with a mixture of pentane and cyclohexane
filtrationthe solid was collected by filtration

Sources & evidence

ORD record: ord-8799f27009a34ac4ba55facae8bd241e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321740B2

Reaction notes

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