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

HRID 2358853Notes

Reaction equation

HRID 2358853 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-ed56849d51f142a08a9a91f307061b96
Source dataset
uspto-grants-2010_07
Patent number
US07763729B2

Reaction notes

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