Water → HCID 13337048, compound

HRID 128402Notes

Reaction equation

HRID 128402 reaction equation
[C:1]([C:3]1[NH:4][C:5]([NH:12][CH2:13][CH2:14][CH3:15])(Cl)[CH:6]=[N:7][C:8]=1[C:9]#[N:10])#[N:2].[CH:16]1[CH:21]=[CH:20][C:19]([CH2:22][SH:23])=[CH:18][CH:17]=1.N1C=CC=CC=1.O>CC(C)=O>[C:9]([C:8]1[C:3]([C:1]#[N:2])=[N:4][C:5]([NH:12][CH2:13][CH2:14][CH3:15])=[C:6]([S:23][CH2:22][C:19]2[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=2)[N:7]=1)#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7509Benzyl mercaptanHCID 20452513HCID 20452513, compound

Product 1

HCID 13337048HCID 13337048, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,3-Dicyano-6-n-propylamino-6-chloropyrazine (1.11 g; 0.005 mole) and 0.87 g (0.007 mole) of benzylthiol were dissolved in 50 ml of acetone. The solution was cooled to 0° to 5° C. With stirring, a solution prepared from 0.40 g (0.005 mole) of pyridine and 20 ml of water was added dropwise over the period of 30 minutes. The mixture was further stirred at 20° to 30° C. for 1 hour, and concentrated under reduced pressure to remove acetone. The residue was extracted with 100 ml of chloform. The extract was washed twice with 50 ml of water, dried over anhydrous calcium chloride, and concentrated under reduced pressure to afford a yellowish solid. Recrystallization of the solid from ethanol afforded 0.47 g (yield 30%) of 2,3-dicyano-5-n-propylamino-6-(benzylthio)pyrazine.

Workup

  1. temperatureThe solution was cooled to 0° to 5° C
  2. additionwas added dropwise over the period of 30 minutes
  3. stirringThe mixture was further stirred at 20° to 30° C. for 1 hour
  4. concentrationconcentrated under reduced pressure
  5. customto remove acetone
  6. extractionThe residue was extracted with 100 ml of chloform
  7. washThe extract was washed twice with 50 ml of water
  8. dry with materialdried over anhydrous calcium chloride
  9. concentrationconcentrated under reduced pressure
  10. customto afford a yellowish solid
  11. customRecrystallization of the solid from ethanol

Sources & evidence

ORD record
ord-96453f032fac4f82ba63c3cf65170adf
Source dataset
uspto-grants-1981_03
Patent number
US04259489

Reaction notes

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