HCID 18467177, compound → HCID 70084300, compound

HRID 2229214Notes

Reaction equation

HRID 2229214 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:15]#[N:16])[N:6]([CH3:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[CH2:1]([O:3][C:4](=[O:17])[C:5]([N:6]([CH3:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[C:15]([NH2:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:2]

Participants

4

Reactant 2

HCID 18467177HCID 18467177, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 70084300HCID 70084300, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl-2-[methyl(phenylmethyl)amino]-cyanoacetate (0.049 mol, 11.3 g) was dissolved in 300 mL of ether and added to 32 mL of 3M PhMgBr, and the resulting mixture was refluxed for 18 h. The reaction was cooled, quenched with sat. NH4Cl solution and extracted with ether. The organics were dried, concentrated, and chromatographed using 1:1 hexanes:ethyl acetate to give 5 g of product. 1H NMR (300 MHz) CDCl3: 7.6-7.2 (m, 10H), 5.01 (s, 1H), 4.27 (t, 2H), 3.59 (s, 2H), 2.73 (t, 2H), 2.31 (s, 3H).

Workup

  1. temperaturethe resulting mixture was refluxed for 18 h
  2. temperatureThe reaction was cooled
  3. customquenched with sat. NH4Cl solution
  4. extractionextracted with ether
  5. customThe organics were dried
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-bef363a99d244fee8d6deedb0e0fd00a
Source dataset
uspto-grants-2002_07
Patent number
US06420383B1

Reaction notes

Loading…