Phenyltrimethylammonium bromide dibromide → Pyridine-2-carbothioamide

HRID 1878936Notes

Reaction equation

HRID 1878936 reaction equation
FC1C=CC=C(F)C=1C(NC1C=CC(C2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[S:16]C=2C)=CC=1)=O.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1.CCO>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:15](=[S:16])[NH2:14]

Participants

5

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 45280533HCID 45280533, compound

Product 1

HCID 1549499Pyridine-2-carbothioamideYield 100.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The solution of 2 (0.5 g, 1.73 mmol) in THF (100 mL) with phenyltrimethylammonium tribromide (0.68 g, 1.8 mmol) was heated at 60° C. for 2 hr. Then the solution was quenched with water and extracted with EtOAc (3×50 mL). The combined EtOAc solution was concentrated to give the crude product, which could be used directly for the next step without further purification. The solution of resulting crude product with pyridine-2-carbothioamide (0.24 g, 1.74 mmol) in EtOH was heated at 70° C. overnight. The solution was diluted with water and extracted with EtOAc. Column chromatography (Hexanes/EtOAc=1/1) afforded compound 2 in 51% overall yield.

Workup

  1. customThen the solution was quenched with water
  2. extractionextracted with EtOAc (3×50 mL)
  3. concentrationThe combined EtOAc solution was concentrated
  4. customto give the crude product, which
  5. customcould be used directly for the next step without further purification

Sources & evidence

ORD record
ord-686a5f8581fd4169be96eb080eee91df
Source dataset
uspto-grants-2012_11
Patent number
US08314130B2

Reaction notes

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