Sulfuric Acid → HCID 19871309, compound

HRID 329694Notes

Reaction equation

HRID 329694 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]#[CH:24])=[C:10]1[C:25]([O:27][CH2:28][CH3:29])=[O:26].S(=O)(=O)(O)[OH:31]>O.O1CCOCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]([CH3:24])=[O:31])=[C:10]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 14547436HCID 14547436, compound

Product 1

HCID 19871309HCID 19871309, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-propyne (1.06 g) [see Preparation 8], mercuric sulphate (0.10 g) and concentrated sulphuric acid (0.2 ml) in a mixture of water (20 ml) and dioxane (20 ml) was heated at 60° for 2 hours and then evaporated. The residue was partitioned between ether and water and the organic layer washed with saturated aqueous sodium chloride solution and water, dried over sodium sulphate and evaporated to give the title compound (0.93 g), m.p. 119°-121°. This material was confirmed spectroscopically to be identical to the product of Preparation 6.

Workup

  1. temperaturewas heated at 60° for 2 hours
  2. customevaporated
  3. customThe residue was partitioned between ether and water
  4. washthe organic layer washed with saturated aqueous sodium chloride solution and water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-90b8d3e6ee6f4e7cbb12d699735e88c9
Source dataset
uspto-grants-1990_01
Patent number
US04892881

Reaction notes

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