Dimethyl Sulfoxide → HCID 54148611, compound

HRID 839630Notes

Reaction equation

HRID 839630 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. (.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 1 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-95aee132ea1042a9a7f5c5aa542159d7
Source dataset
uspto-grants-1978_06
Patent number
US04096264

Reaction notes

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