Ethanol → HCID 68950700, compound

HRID 1452455Notes

Reaction equation

HRID 1452455 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([OH:18])[CH3:17].CCCCCC.CCOCC>C(Cl)Cl>[CH2:1]([C:8]1[CH:9]=[C:10]([C:11](=[NH:12])[O:18][CH2:16][CH3:17])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 21584099Diethylether hexaneHCID 21685088HCID 21685088, compound

Product 1

HCID 68950700HCID 68950700, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-4 °C

Procedure

Anhydrous hydrochloric acid was gently bubbled for 90 minutes into a solution containing 3-benzylbenzonitrile (1.0 g, 5.2 mmol) and absolute ethanol (0.45 mL, 7.8 mmol) in methylene chloride (7 mL) maintained at −4° C. After standing at 4° C. for a week, the reaction mixture was poured into 2:1 hexane/ether (500 mL), left at room temperature for 15 minutes and filtered. The residue was washed with 2:1 hexane/ether (50 mL) and dried in vacuo at room temperature. Yield 1.1 g (77 percent). mp 121-122° C.; 1H NMR (CDCl3) δ 12.58 (br, 1H), 8.29-8.25 (m, 2H), 7.49-7.44 (m, 2H), 7.32-7.27(m, 2H), 7.22-7.18(m, 3H), 4.93 (q, J=6.9 Hz, 2H), 4.09 (s, 2H), 1.60 (t, J=6.9 Hz, 3H); EI/MS 240 m/e (M+1);

Workup

  1. customAnhydrous hydrochloric acid was gently bubbled for 90 minutes into a solution
  2. waitAfter standing at 4° C. for a week
  3. filtrationfiltered
  4. washThe residue was washed with 2:1 hexane/ether (50 mL)
  5. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-91b1c25938eb44e0992fc278b675d6df
Source dataset
uspto-grants-2009_01
Patent number
US07473669B2

Reaction notes

Loading…