Dichloromethane → HCID 178466742, compound

HRID 1161755Notes

Reaction equation

HRID 1161755 reaction equation
CN(C=C(C(=O)C1C=CC=CC=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O)C.[C:23]([CH2:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:33])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.COC([O:47][CH3:48])N(C)C.[CH2:49](Cl)Cl>>[CH2:48]([O:47][C:12]1[CH:11]=[CH:10][C:9]([NH:8][CH:6]=[C:31]([C:23](=[O:30])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:33])=[CH:14][CH:13]=1)[CH3:49]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 703983-Oxo-3-phenylpropionanilideHCID 78373Dimethylformamide dimethyl acetalHCID 86609726HCID 86609726, compound

Product 1

HCID 178466742HCID 178466742, compoundYield 61%

Procedure

α-[(Dimethylamino)methylene]-β-oxo-N-phenylbenzenepropanamide. A solution of 2-benzoylacetanilide (Aldrich; 1.088 g, 4.55 mmol) in 15 mL of CH2Cl2 was treated with neat N,N-dimethylformamide dimethyl acetal (0.75 mL, 670 mg, 5.63 mmol). The reaction was allowed to stir at rt overnight. Concentration in vacuo gave a solid that was adsorbed onto 3.3 g of silica gel and added to 17 cm of flash silica gel in a 5 cm dia. column. Elution with 2 L of 4:1 EtOAc/hexanes afforded 797 mg (61%) of the desired compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.70 (br s, 1H), 7.64 (d, 2H, J=8.1 Hz), 7.59 (d, 2H, J=7.3 Hz), 7.48 (t, 1H, J=6.8 Hz), 7.44 (s, 1H), 7.42 (t, 1H, J=7.0 Hz), 7.30 (t, 2H, J=8.0 Hz), 7.04 (t, 1H, J=7.3 Hz), 3.01 (br s, 6H).

Workup

  1. concentrationConcentration in vacuo
  2. customgave a solid
  3. additionadded to 17 cm of flash silica gel in a 5 cm dia
  4. washElution with 2 L of 4:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-c55432a55268421594c6bac2287bbccb
Source dataset
uspto-grants-2010_10
Patent number
US07820663B2

Reaction notes

Loading…