Dimethyl Sulfoxide → HCID 20095251, compound

HRID 1770075Notes

Reaction equation

HRID 1770075 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[N:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13]=2[C:14]([O:16]C)=[O:15])[N:4]=1.CS(C)=O.[OH-].[Na+]>O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[N:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13]=2[C:14]([OH:16])=[O:15])[N:6]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 15767484HCID 15767484, compound

Product 1

HCID 20095251HCID 20095251, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.6 g (0.007 mol) of methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-4-phenylnicotinate and 50 ml of dimethylsulfoxide were weighed, and 4.6 ml (0.009 mol) of 2N sodium hydroxide aqueous solution was added dropwise thereto at 60° C. After the dropwise addition, the resultant mixture was further stirred for 30 minutes at 60° C. The resultant mixture was poured into water, and was washed twice with ethyl acetate. The aqueous layer was then adjusted to pH 2 with 10% hydrochloric acid aqueous solution, and the precipitated crystal was filtrated out. The crystal thus obtained was washed with water, and was then dried. The dried crystal was recrystallized with ethyl acetate to obtain 1.1 g of a white crystal.

Workup

  1. customat 60° C
  2. additionAfter the dropwise addition
  3. washwas washed twice with ethyl acetate
  4. filtrationthe precipitated crystal was filtrated out
  5. customThe crystal thus obtained
  6. washwas washed with water
  7. customwas then dried
  8. customThe dried crystal was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-76827752c7d043c3b3b608cc506ec757
Source dataset
uspto-grants-1995_01
Patent number
US05385880

Reaction notes

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