1,2-Dichloroethane → HCID 68869577, compound

HRID 1986386Notes

Reaction equation

HRID 1986386 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[C:4]([O:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:3]=1.[C:20]([CH2:22][C:23](O)=[O:24])#[N:21].C(Cl)CCl.C(N(CC)CC)C>C1COCC1>[NH2:1][C:2]1[C:7]([NH:8][C:23](=[O:24])[CH2:22][C:20]#[N:21])=[CH:6][N:5]=[C:4]([O:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 68869859HCID 68869859, compound

Product 1

HCID 68869577HCID 68869577, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 3 in THF (150 mL), was added cyanoacetic acid (870 mg, 10.2 mmol), EDC (4.32 g, 22.5 mmol) and triethylamine (8 ml, 51 mmol). This mixture was then stirred at rt for overnight. The reaction mixture was concentrated, taken up in EtOAC (300 mL), washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The residue was dissolved in AcOH (100 ml), and then heated to 115° C. for 24 h. The reaction mixture was concentrated to afford the title compound, which was used directly to next step without further purification. MS (ES+) m/e 309 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in AcOH (100 ml)
  7. temperatureheated to 115° C. for 24 h
  8. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-577d2f645f2646e190d3f5cbee4e996f
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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