Ethanethiol → 3-ethylsulfanyl-9-oxo-9H-indeno[1,2-b]pyrazine-2-carbonitrile

HRID 240313Notes

Reaction equation

HRID 240313 reaction equation
[CH2:1]([SH:3])[CH3:2].[OH-].[Na+].Cl[C:7]1[N:12]=[C:11]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19](=[O:20])[C:10]2=[N:9][C:8]=1[C:21]#[N:22]>C1COCC1>[CH2:1]([S:3][C:7]1[N:12]=[C:11]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19](=[O:20])[C:10]2=[N:9][C:8]=1[C:21]#[N:22])[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 14798Sodium HydroxideHCID 160653593-chloro-9-oxo-9H-indeno[1,2-b]pyrazine-2-carbonitrile

Product 1

HCID 160657793-ethylsulfanyl-9-oxo-9H-indeno[1,2-b]pyrazine-2-carbonitrileYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethanethiol (62 μl, 0.84 mmol) and 1N NaOH (0.5 ml, 0.5 mmol) in THF (2.1 ml) 9 (101 mg, 0.42 mmol) was added. The mixture was stirred at room temperature for 30 min then the solvent was evaporated under reduced pressure. The residue was dissolved in H2O (4 ml) and extracted with CH2Cl2 (2×4 ml). The collected organic phases were dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography (CH2Cl2) affording 23 (98 mg, 87%) as orange solid.

Workup

  1. additionwas added
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in H2O (4 ml)
  4. extractionextracted with CH2Cl2 (2×4 ml)
  5. dry with materialThe collected organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-7978118e8c2d401486b1a20211b9884a
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

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