Water → Pyridine-2-carbothioamide

HRID 1682425

Reaction equation

HRID 1682425 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[NH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=O.O>O1CCCC1>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16](=[S:2])[NH2:15]

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 150702-Pyridinecarboxamide

Product 1

HCID 1549499Pyridine-2-carbothioamideYield 74.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

43 g of phosphorus pentasulfide were added slowly to 46.8 g of the amide of Stage A in 700 ml of tetrahydrofuran and the mixture was stirred for 4 hours at ambient temperature. The reaction mixture was poured into water and extracted with ether. The extracts were dried and the solvent was evaporated under reduced pressure. After chromatography on silica (eluant: CH2Cl2 --AcOEt 8-2), 10 g of expected product melting at 137° C. were obtained.

Workup

  1. extractionextracted with ether
  2. customThe extracts were dried
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-189d08015cd14c07b7bc2532edc628c1
Source dataset
uspto-grants-1997_06
Patent number
US05635485

Linked notes

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