Phenyl Isothiocyanate → HCID 178462481, compound

HRID 1925171Notes

Reaction equation

HRID 1925171 reaction equation
[NH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:17])[N:13]([CH2:15][CH3:16])[CH:14]=2)=[CH:5][CH:4]=1)[NH2:2].N(C1C=CC=CC=1)=[C:19]=[S:20]>CN1C(=O)CCC1.C(Cl)Cl>[SH:20][C:19]1[N:8]2[CH:7]=[C:6]([C:9]3[CH:10]=[CH:11][C:12](=[O:17])[N:13]([CH2:15][CH3:16])[CH:14]=3)[CH:5]=[CH:4][C:3]2=[N:1][N:2]=1

Participants

5

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 592332085-(6-hydrazinylpyridin-3-yl)-1-ethylpyridin-2(1H)-one

Product 1

HCID 178462481HCID 178462481, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5-(6-hydrazinylpyridin-3-yl)-1-ethylpyridin-2(1 H)-one (1.2 g, 5.22 mmol) and isothiocyanatobenzene (775 mg, 5.74 mmol) in NMP(3 ml) and DCM (10 ml) was stirred at room temperature for 30 min. The DCM was removed via rotary evaporation and the reaction was diluted with 1,3-dichlorobenzene (7 mL). The mixture was then heated in a microwave at 160° C. for 1 hr. Ether (10 ml) was added to the reaction and the resulting solid was collected by filtration and washed with ether to provide the title compound, 5-(3-mercapto-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-ethylpyridin-2(1 H)-one (600 mg, 42.3% yield).

Workup

  1. customThe DCM was removed via rotary evaporation
  2. additionthe reaction was diluted with 1,3-dichlorobenzene (7 mL)
  3. temperatureThe mixture was then heated in a microwave at 160° C. for 1 hr
  4. additionEther (10 ml) was added to the reaction
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-15f5a1c3e74d429196390a6d336649cd
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

Loading…