Dimethyl Sulfoxide → HCID 12345094, compound

HRID 1195616Notes

Reaction equation

HRID 1195616 reaction equation
CS([C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:13][CH:12]=2)=[CH:7][N:6]=1)(=O)=O.[C-:23]#[N:24].[Na+].CS(C)=O>O>[C:23]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:13][CH:12]=2)=[CH:7][N:6]=1)#[N:24]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 12345087HCID 12345087, compound

Product 1

HCID 12345094HCID 12345094, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound (XI) (1.8 g, 0.006 mol) and NaCN (0.275 g, 0.006 mol) were added to dimethylsulfoxide (5 ml), followed by mixing at 100° C. for one hour, allowing the resulting material to cool, adding water (15 ml), filtering off the resulting crystals and recrystallizing crystals from ethanol to obtain 2-cyano-5-(4-pentyloxyphenyl)pyrimidine (XII) (0.7 g) (yield: 47%) having a melting point of 100° C.

Workup

  1. additionby mixing at 100° C. for one hour
  2. temperatureto cool
  3. filtrationfiltering off the resulting crystals
  4. customrecrystallizing crystals from ethanol

Sources & evidence

ORD record
ord-a767329483a54ec3be1212392ed9d451
Source dataset
uspto-grants-1992_05
Patent number
US05112523

Reaction notes

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