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Benzyl mercaptan → 3-Pyridinecarbonitrile, 2-[(phenylmethyl)thio]-

HRID 20248
Notes
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Reaction equation

HRID 20248 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16]([SH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[C:17]1([CH2:16][S:23][C:2]2[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 810792-Chloronicotinonitrile

Product 1

HCID 5012383-Pyridinecarbonitrile, 2-[(phenylmethyl)thio]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

85 g of 2-chloro-3-cyanopyridine, 98.2 g potassium carbonate anhydrous powder and 600 g of dimethyl formamide were mixed to obtain a suspension. To this suspension, a solution of 79.2 g benzyl mercaptan in 250 ml dimethyl formamide was added dropwise over a period of approx. 3 hours at 80-90° C. The reaction mass was agitated for 2 hours at the same temperature. The temperature was slowly raised to 120° C. Then, the reaction mixture was reacted at 120-130° C. for about 1.5 hours. Afterwards, heating was stopped and reaction mass was allowed to attain the room temperature. Inorganic cake was separated by filtration. Dimethyl formamide was distilled under reduced pressure, and the residue left at bottom was 2-(phenyl methyl thio)-3-cyano pyridine 150 g, sufficiently pure to be used in the next step.

Workup

  1. customto obtain a suspension
  2. customThen, the reaction mixture was reacted at 120-130° C. for about 1.5 hours
  3. temperatureAfterwards, heating
  4. customreaction mass
  5. customthe room temperature
  6. customInorganic cake was separated by filtration
  7. distillationDimethyl formamide was distilled under reduced pressure
  8. waitthe residue left

Sources & evidence

ORD record
ord-cbcd9c92fadd44968fde6c4bac74bf3e
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745631B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes