Water → HCID 19428091, compound

HRID 1078551Notes

Reaction equation

[H-].[Na+].[N:3]1[C:8]2[S:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[NH:12][C:13](=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:19](I)[CH3:20].O>CN(C)C=O>[CH2:19]([N:12]1[C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[S:9][C:8]2[N:3]=[CH:4][CH:5]=[CH:6][C:7]=2[C:13]1=[O:14])[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydride (1.05 g of a 50% suspension in mineral oil) was added to a suspension of pyrido[2,3-b][1,5]benzothiazepin-5(6H)-one (4.0 g, 0.0175 mol) in 100 ml of dimethylformamide and the resulting mixture stirred until the evolution of gas stopped, at which time the mixture was heated to 50° C. for 30 min. After cooling to room temperature, ethyl iodide (5.46 g, 0.035 mol) was slowly added and the reaction mixture allowed to stir for 2 hours. Crushed ice was added to decompose unreacted sodium hydride. Water was then added and the product was extracted with ether, dried (anhydrous sodium sulfate) and concentrated in vacuo. After washing the solid residue with hexane, it was recrystallized from ethyl acetate/hexane to give 0.66 g (14% of theory) of product as yellow crystals, m.p. 148°-149° C.

Workup

temperatureAfter cooling to room temperature
stirringto stir for 2 hours
additionCrushed ice was added
extractionthe product was extracted with ether
dry with materialdried (anhydrous sodium sulfate)
concentrationconcentrated in vacuo
washAfter washing the solid residue with hexane, it
customwas recrystallized from ethyl acetate/hexane
customto give 0.66 g (14% of theory) of product as yellow crystals, m.p. 148°-149° C.

Sources & evidence

ORD record: ord-144298a259e240d08b3959031a39dd9a
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05550122

Reaction notes

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