Methane → HCID 19050642, compound

HRID 863744Notes

Reaction equation

HRID 863744 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[O:10])[O:8][C:7]2(C#N)[C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=1.[OH-].[Na+].C1C[O:29]CC1.C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[O:10])[O:8][C:7]2([OH:29])[C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19050667HCID 19050667, compound

Product 1

HCID 19050642HCID 19050642, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.8 g of 7-chloro-3-cyano-3-(4,6-dimethoxy-2-pyrimidinyl)phthalide, 50 ml of 1% NaOH and 50 ml of THF are stirred at room temperature for 3 hrs. The THF is removed by evaporation and the mixture is diluted with water and extracted twice with ethyl acetate. The aqueous solution is acidified with 2N--H2SO4. The resulting acid solution is extracted with 3×100 ml ethyl acetate and the organic phases combined, dried over Na2SO4 and concentrated to give a pale yellow solid. This residue is taken up in ethyl acetate and treated with activated charcoal until the yellow base line material is removed to give the title product as a white solid m.p. 188°-190° C.

Workup

  1. customThe THF is removed by evaporation
  2. additionthe mixture is diluted with water
  3. extractionextracted twice with ethyl acetate
  4. extractionThe resulting acid solution is extracted with 3×100 ml ethyl acetate
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give a pale yellow solid
  8. customis removed

Sources & evidence

ORD record
ord-f978f063ffd3434c8bddec7bc53fd0af
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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