Sulfuric Acid → HCID 67544025, compound

HRID 2176110Notes

Reaction equation

Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[CH3:11][NH+:12]1[C@@H:17]2[CH2:18][C:19]([CH2:21][C@H:13]1[CH2:14][CH2:15][CH2:16]2)=O.S(=O)(=O)(O)O>O1CCOCC1>[CH3:10][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:15]1[CH2:16][CH:17]3[N:12]([CH3:11])[CH:13]([C:14]2=1)[CH2:21][CH2:19][CH2:18]3

Participants

Conditions

Temperature: 80 °C

Procedure

In a 100 mL round-bottom flask were combined p-tolylhydrazine hydrochloride (1.58 g, 10 mmol; Aldrich), pseudopelletierine hydrochloride (2.0 g, 10.5 mmol; Acros), and concentrated sulfuric acid (5 mL) in dioxane (50 mL). The reaction mixture was heated to 80° C. for 2.5 hours, then cooled to room temperature. The solvent was decanted, and the residue was dissolved in water (20 mL) and basified with solid potassium carbonate to pH ˜12. This solution was extracted with dichloromethane (3×50 mL), and the combined organic phases were dried over magnesium sulfate. After removing the solvent under vacuum, the resulting solid was recrystallized from ether to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.21-1.41 (m, 2H), 1.60-1.71 (m, 2H), 1.90-2.08 (m, 2H), 2.35 (s, 3H), 2.38 (s, 3H), 2.42-2.52 (m, 1H), 3.16-3.27 (m, 2H), 4.09 (t, J=3 Hz, 1H), 6.86 (dd, J=8, 1 Hz, 1H), 7.10 (s, 1H), 7.17 (d, J=8 Hz, 1H); MS (DCI/NH3) m/z 241 (M+H)+.

Workup

customIn a 100 mL round-bottom flask were combined
temperaturecooled to room temperature
customThe solvent was decanted
dissolutionthe residue was dissolved in water (20 mL)
extractionThis solution was extracted with dichloromethane (3×50 mL)
dry with materialthe combined organic phases were dried over magnesium sulfate
customAfter removing the solvent under vacuum
customthe resulting solid was recrystallized from ether

Sources & evidence

ORD record: ord-0dc2ecd0a9dd48f893a8cae0f310a14f
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09063126B2

Reaction notes

Loading…