Sulfuric Acid → HCID 19871309, compound

HRID 569596Notes

Reaction equation

HRID 569596 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), mercuric sulphate (0.10 g) and concentrated sulphuric acid (0.2 ml) in a mixture of water (20 ml) and dioxane (20ml) 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 compund (0.93 g), m.p. 119°-121°. This material was confirmed spectroscopically to be idetnical 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
  7. customto give the title compund (0.93 g), m.p. 119°-121°
  8. customto be idetnical to the product of preparation 6

Sources & evidence

ORD record
ord-35d33c08f48f4412ad6f2bdde73aa748
Source dataset
uspto-grants-1988_03
Patent number
US04732985

Reaction notes

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