Acetic Acid → HCID 18320684, compound

HRID 1699531Notes

Reaction equation

HRID 1699531 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([C:13]#[N:14])=[C:11]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:24])[CH:16]=2)[N:10]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27](C(OCC(Cl)(Cl)Cl)=O)[CH:26]=2)[C:9]1=[O:42])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.O.C(OCC)(=O)C>CN(C=O)C.[Zn].[Cl-].[Cd+2].[Cl-]>[C:1]([O:5][C:6]([N:8]1[C:12]([C:13]#[N:14])=[C:11]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:24])[CH:16]=2)[N:10]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)[C:9]1=[O:42])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 18320756HCID 18320756, compound

Product 1

HCID 18320684HCID 18320684, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24633Cadmium chloride, dihydrateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.26 g (0.41 mmol) of the product from step b) in 5 ml of DMF was added 0.27 g (4.1 mmol) zinc powder, 0.028 g (0.12 mmol) of cadmium chloride and 5 ml of acetic acid. The mixture was sonicated for 2 minutes and stirred at room temperature for 30 minutes. Water and ethyl acetate were added, the phases were separated and the organic phase washed with saturated NaHCO3(aq), dried over Na2SO4 and evaporated. The residue was purified by chromatography on SiO2 (toluene:ethyl acetate) fuishing the sub-title compound (150 mg, 80%).

Workup

  1. customThe mixture was sonicated for 2 minutes
  2. customthe phases were separated
  3. washthe organic phase washed with saturated NaHCO3(aq)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by chromatography on SiO2 (toluene:ethyl acetate)

Sources & evidence

ORD record
ord-e7b2d323189e4bbaabfa10184933430d
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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