Ethanol → Sodium 3-cyano-1-(2-methylphenyl)-6-oxo-1,6-dihydropyridine-2-thiolate

HRID 30421Notes

Reaction equation

HRID 30421 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+:10].[C:11]1([CH3:20])[C:12]([N:17]=[C:18]=[S:19])=[CH:13][CH:14]=[CH:15][CH:16]=1.[C:21](#[N:23])[CH3:22].[CH3:24][CH2:25][OH:26]>C1COCC1>[C:21]([C:22]1[CH:1]=[CH:24][C:25](=[O:26])[N:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH3:20])[C:18]=1[S-:19])#[N:23].[Na+:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 6342AcetonitrileHCID 691952-Methylphenyl isothiocyanateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 68457473Sodium 3-cyano-1-(2-methylphenyl)-6-oxo-1,6-dihydropyridine-2-thiolate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium bis(trimethylsilyl)amide (84 mL of a 1.0M solution in THF, 84 mmol) was added to a solution of o-tolyl isothiocyanate (5.0 g, 33.5 mmol) and acetonitrile (18 mL, 0.345 mol) in THF (100 mL) at −78° C. The mixture was allowed to warm to r.t. over 3 h. N,N-Dimethyluracil (4.62 g, 33 mmol) and EtOH (75 mL) were added and the mixture heated at reflux for 3 h then stirred at r.t. overnight. Volatiles were removed in vacuo. The residue was used crude in the next step without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 h
  3. customVolatiles were removed in vacuo
  4. customwithout further purification

Sources & evidence

ORD record
ord-cc22350c754c4ebeb8418a0e9af4d054
Source dataset
uspto-grants-2008_09
Patent number
US07423047B2

Reaction notes

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