Potassium Carbonate → 3-(3-(5-Cyanopentylthio)-1,2,5-thiadiazol-4-yl)pyridine

HRID 963112Notes

Reaction equation

HRID 963112 reaction equation
O.[SH2:2].[Na].Cl[C:5]1[C:9]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:8][S:7][N:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[N:29]>CN(C=O)C.O>[C:28]([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][S:2][C:5]1[C:9]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:8][S:7][N:6]=1)#[N:29]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 810936-BromohexanenitrileHCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazoleHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 196125283-(3-(5-Cyanopentylthio)-1,2,5-thiadiazol-4-yl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydrogen sulfide monohydrate (0.25 g, 3.3 mmol) was added to a solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)pyridine (0.59 g, 3.0 mmol) in DMF (20 ml) at room temperature and the reaction mixture was stirred for 1 h. Potassium carbonate (1.24 g, 9 mmol) and 6-bromocapronitrile (0.80 g, 4.5 mmol) were added and the reaction mixture was stirred for additionally 24 h. Water (50 ml) was added and extracted with ether. The combined ether phases were dried and evaporated to give the title compound.

Workup

  1. stirringthe reaction mixture was stirred for additionally 24 h
  2. extractionextracted with ether
  3. dry with materialThe combined ether phases were dried
  4. customevaporated

Sources & evidence

ORD record
ord-c9a69c1babd1464982226f437d8e9079
Source dataset
uspto-grants-1998_06
Patent number
USRE035822

Reaction notes

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