HCID 18467182, compound → HCID 70089236, compound

HRID 2229216Notes

Reaction equation

HRID 2229216 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:14]#[N:15])[N:6]([CH3:13])[CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].[C:17]1([Mg]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC>[CH2:1]([O:3][C:4](=[O:16])[C:5]([N:6]([CH3:13])[CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)=[C:14]([NH2:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:2]

Participants

4

Reactant 2

HCID 18467182HCID 18467182, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 70089236HCID 70089236, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl-2-[methyl(thienylmethyl)amino]-cyanoacetate (0.014 mol, 3.4 g) was dissolved in 100 mL of ether and added to 9.5 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 1.4 g of product. 1H NMR (300 MHz) CDCl3: 7.58 (d, 2H), 7.4 (m, 3H), 7.21 (d, 1H), 6.89 (m, 2H), 5.0 (s, 1H), 4.28 (t, 2H), 3.85 (s, 2H), 2.75 (t, 2H), 2.38 (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-ece3c9aa844c4e2294e4a7b1f26d265f
Source dataset
uspto-grants-2002_07
Patent number
US06420383B1

Reaction notes

Loading…