Sodium Bicarbonate → HCID 86598135, compound

HRID 860689Notes

Reaction equation

HRID 860689 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=1.C(N)(=[S:18])C.C(=O)(O)[O-].[Na+]>Cl.O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]([NH2:13])=[S:18])=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723949ThioacetamideHCID 46312076HCID 46312076, compound

Product 1

HCID 86598135HCID 86598135, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(2-Fluoro-phenyl)-nicotinonitrile (9.8 g, 49.4 mmol) and thioacetamide (5.94 g, 79.1 mmol) in 4.0 M HCl in dioxane (200 mL) is heated at 100° C. for 3 days, cooled to room temperature. The raction mixture is poured into old saturated sodium bicarbonate and stirred for 30 min. Solid product is collected by filtration and dried under vacuum giving the title compound (11.4 g).

Workup

  1. temperaturecooled to room temperature
  2. filtrationSolid product is collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d87a0ee1c1e8403cb26de3720e79781c
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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