Sodium Carbonate → HCID 9926729, compound

HRID 2054717Notes

Reaction equation

HRID 2054717 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:13])[CH3:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35])(OCC)=O>O.C(#N)C>[C:26]1(=[O:35])[N:13]([CH:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:12])[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 31592431-(3,4-Dimethoxyphenyl)ethan-1-amine

Product 1

HCID 9926729HCID 9926729, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-Phthalimido-1-(31, 4′-dimethoxyphenyl)ethane. To a stirred solution of 1-(3′,4′-dimethoxyphenyl)ethylamine (1.81 grams, 10.0 mmol) and sodium carbonate (1.14 grams, 10.8 mmol) in a mixture of water (80 miilliters) and acetonitrile (50 milliliters) was add N-carbethoxyphthalimide (2.19 grams, 10 mmol). The resulting suspension was stirred for 3.5 hours at room temperature and the filtered to afford 1.24 grams (40%) of the crude product as a white powder. The crude product was recrystallized from hexane/ethyl acetate and dried in vacuo (60° C., <1 mm) to afford 0.85 grams (27%) of the product as white crystals: mp 124-125° C.; 1H NMR (CDCl3) δ 7.96-7.78 (m, 4H), 7.09-6.81 (m, 3H), 5.40 (q, J=7.2 Hz, 1H), 3.73 (s, 3H), 3.72 (s, 3H), 1.81 (d, J=7.2 Hz, 3H); 13C NMR (DMSO-d6) δ 167.6, 148.4, 148.0, 134.4, 132.9, 131.3, 122.9, 118.8, 111.5, 110.8, 55.4, 48.6, 17.7. Anal. Calculated for C18H17NO4. Theoretical: C, 69.44; H, 5.50; N, 4.50. Found: C, 69.63; H, 5.45; N, 4.42. HPLC 100%.

Workup

  1. filtrationthe filtered
  2. customto afford 1.24 grams (40%) of the crude product as a white powder
  3. customThe crude product was recrystallized from hexane/ethyl acetate
  4. customdried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-6fe47f2097d94e5fb570433c3fe96cac
Source dataset
uspto-grants-2008_02
Patent number
US07329761B2

Reaction notes

Loading…