Ethanethiol → HCID 13560232, compound

HRID 637802Notes

Reaction equation

HRID 637802 reaction equation
[OH-].[Na+].[CH2:3]([SH:5])[CH3:4].Cl[C:7]1[C:12]([C:13]#[N:14])=[CH:11][C:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)=[CH:9][N:8]=1>C1COCC1>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[Cl:22])[O:15][C:10]1[CH:11]=[C:12]([C:13]#[N:14])[C:7]([S:5][CH2:3][CH3:4])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6343Ethanethiol2×HCID 14798Sodium Hydroxide2×HCID 13560231HCID 13560231, compound

Product 1

HCID 13560232HCID 13560232, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

THF (25 ml), and NaOH (0.8 g) were mixed in a reaction flask to which was added 1.24 g of ethanethiol (previously chilled in an ice-salt bath). This mixture was stirred at room temperature until all of the NaOH was dissolved. Separately, 4.5 g of 2-chloro-5-(3,4-dichlorophenoxy)-3-pyridinecarbonitrile was dissolved in 25 ml of THF and then added to the previously prepared ethanethiol mixture. This combination was then stirred at room temperature for 30 minutes and then heated to boiling for 2 hours after which it was allowed to cool and then poured into 300 g of ice. A precipitate formed which was collected by filtration and subsequently recrystallized from a CH2Cl2 /hexane mixture to give 4.3 g of the desired 5-(3,4-dichlorophenoxy)-2-ethylthio-3-pyridinecarbonitrile, m.p. 80°-81° C.

Workup

  1. temperaturepreviously chilled in an ice-salt bath)
  2. dissolutionwas dissolved
  3. temperatureheated
  4. waitto boiling for 2 hours
  5. temperatureto cool
  6. customA precipitate formed which
  7. filtrationwas collected by filtration
  8. customsubsequently recrystallized from a CH2Cl2 /hexane mixture

Sources & evidence

ORD record
ord-9fbc3688e67443fe8a0f651334b95e24
Source dataset
uspto-grants-1985_12
Patent number
US04558134

Reaction notes

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