Dimethyl Sulfoxide → HCID 54148611, compound

HRID 1447604Notes

Reaction equation

HRID 1447604 reaction equation
[C-:1]#[N:2].[Na+].CS(C)=O.[CH3:8][O:9][C:10]([NH:12][C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][C:18]([S:21][C:22]3[CH:27]=[CH:26][C:25](OC(=O)C)=[CH:24][CH:23]=3)=[CH:17][N:16]2[CH:32]=1)=[O:11].CS(C)([O-])=O>O>[C:1]([C:25]1[CH:24]=[CH:23][C:22]([S:21][C:18]2[CH:19]=[CH:20][C:15]3[N:16]([CH:32]=[C:13]([NH:12][C:10]([O:9][CH3:8])=[O:11])[N:14]=3)[CH:17]=2)=[CH:27][CH:26]=1)#[N:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 53698142HCID 53698142, compoundHCID 178504152HCID 178504152, compound

Product 1

HCID 54148611HCID 54148611, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.7 g. of cuprous cyanide and 2.6 g. of finely powdered sodium cyanide in 20 ml. of dimethyl sulfoxide is treated dropwise with a solution of 4.12 g. (0.01 mole) of the diazonium tetrafluoroborate salt of 6-(aminophenylthio)-2-(methoxycarbonylamino) imidazo [1,2-a] pyridine obtained in Example 15 in 10 ml. of dimethyl sulfinate. An exotherm is observed and external cooling is necessary. The reaction mixture is stirred at room temperature for one hour, diluted with water and the solids collected by filtration. The solids are washed with water, dried and recrystallized from dimethylformamide-ethanol (50/50) to yield 6-(p-cyanophenylthio)-2-(methoxycarbonylamino) imidazo [1,2-a] pyridine.

Workup

  1. temperatureexternal cooling
  2. filtrationthe solids collected by filtration
  3. washThe solids are washed with water
  4. customdried
  5. customrecrystallized from dimethylformamide-ethanol (50/50)

Sources & evidence

ORD record
ord-521ede13a547479f92af1f7050fa49ec
Source dataset
uspto-grants-1979_12
Patent number
US04177274

Reaction notes

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