Propionyl chloride → HCID 19065153, compound

HRID 265335Notes

Reaction equation

HRID 265335 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:12]=[CH:11][CH:10]=[N:9]2)=[CH:4][C:3]=1[SH:13].[C:14](Cl)(=O)[CH2:15][CH3:16].C(=O)([O-])O.[Na+]>CN1CCCC1=O>[CH2:15]([C:16]1[S:13][C:3]2[CH:4]=[C:5]([N:8]3[N:9]=[CH:10][CH:11]=[N:12]3)[CH:6]=[CH:7][C:2]=2[N:1]=1)[CH3:14]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 136120203HCID 136120203, compound

Product 1

HCID 19065153HCID 19065153, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

The 2-amino-5-(1,2,3-triazol-2-yl)-thiophenol (2.3 g) was dissolved in N-methylpyrrolidone (8 ml), and propionyl chloride (0.472 ml) was added to the solution, followed by heating and stirring at 70° C. for 5 hours. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, and subjected to extraction with dichloromethane. The resultant organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure and then purified through a silica gel column (hexane-ethyl acetate=4:1→1:1), thereby obtaining the intended compound, 2-ethyl-6-(1,2,3-triazol-2-yl)benzothiazole (940 mg). Physical properties of this product are described below.

Workup

  1. temperatureby heating
  2. extractionsubjected to extraction with dichloromethane
  3. dry with materialThe resultant organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified through a silica gel column (hexane-ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-5a031fb7f479419ea845a367f798dda7
Source dataset
uspto-grants-1997_07
Patent number
US05648372

Reaction notes

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