Sulfuric Acid → HCID 14458720, compound

HRID 1651037Notes

Reaction equation

HRID 1651037 reaction equation
[C:1](OCC)(=O)CC(OCC)=O.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH3:23])[N:18]=[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[N:25]=2)[N:16]=1.[OH-].[Na+].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O.CO.O1CCCC1>[Cl:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[O:30][C:26]1[N:25]=[C:24]([C:17]2[N:16]=[C:15]([CH3:1])[CH:20]=[C:19]([CH2:21][CH2:22][CH3:23])[N:18]=2)[CH:29]=[CH:28][CH:27]=1

Participants

10

Reactant 6

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 14458719HCID 14458719, compound

Product 1

HCID 14458720HCID 14458720, compoundYield 76.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To tetrahydrofuran (30 ml) were added diethyl malonate (1.35 g) and 60% oilly sodium hydride (0.34 g), and then 4-chloro-2-(6-o-chlorophenoxy-2-pyridinyl)-6-n-propylpyrimidine (2 g). The mixture was heated under refluxing for 30 minutes. Sodium hydroxide (0.72 g) solution in water (10 ml) and methanol (10 ml) were added thereto, and the mixture was further heated under refluxing for 20 minutes. After the mixture was left to stand until it was cooled to room temperature, sulfuric acid (1.2 g) was added dropwise thereto. The mixture was heated under refluxing for 30 minutes and left to stand to room temperature. 1-N aqueous sodium carbonate solution was added until a mixture was neutralized, and concentrated under reduced pressure. The residue was subjected to silica-gel column chromatography (eluent; n-hexane: ethyl acetate=2:1 in volume) to give 2-(6-o-chlorophenoxy-2-pyridinyl)-4-methyl-6-n-propylpyrimidine (1.45 g, yield 74%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for 30 minutes
  3. temperaturethe mixture was further heated
  4. temperatureunder refluxing for 20 minutes
  5. waitAfter the mixture was left
  6. temperatureThe mixture was heated
  7. temperatureunder refluxing for 30 minutes
  8. waitleft
  9. customto stand to room temperature
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b53cc1014ce41259914fdcc097329b9
Source dataset
uspto-grants-1990_05
Patent number
US04927827

Reaction notes

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