18-Crown-6 → 7-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-thiocyano-phthalide

HRID 22162

Reaction equation

HRID 22162 reaction equation
Cl[CH:2]1[C:11]2[C:6](=[C:7]([O:12][C:13]3[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=3)[CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1.[S-:23][C:24]#[N:25].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH3:22][O:21][C:15]1[CH:16]=[C:17]([O:19][CH3:20])[N:18]=[C:13]([O:12][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[C:4](=[O:5])[O:3][CH:2]3[S:23][C:24]#[N:25])[N:14]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 516872Potassium thiocyanateHCID 199274063-Chloro-7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-phthalide

Product 1

HCID 199274197-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-thiocyano-phthalide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.4 g of 3-chloro-7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-phthalide (see Example 85) and 0.46 g of potassium thiocyanate is heated in the presence of a spatula tip of 18-crown-6 in 15 ml of acetonitrile for 4 hours. The mixture is then filtered through Celite®, concentrated by evaporation and chromatographed with 30% ethyl acetate/n-hexane to yield 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-thiocyano-phthalide in the form of light-yellow crystals, m.p. 161°-163° C.

Workup

  1. filtrationThe mixture is then filtered through Celite®
  2. concentrationconcentrated by evaporation
  3. customchromatographed with 30% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e1efd6f1d85b460595d8335948a61130
Source dataset
uspto-grants-1995_06
Patent number
US05428002

Linked notes

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