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

HRID 1455528Notes

Reaction equation

HRID 1455528 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.[CH3:21][C:22]#[N:23].[CH3:24][CH2:25][OH:26]>C1COCC1>[C:22]([C:21]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 NaHMDS (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 MeCN (18 mL) in THF (100 mL) at −78° C. The mixture was allowed to warm to r.t. over 3h. 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-5c45dacdd42249a2bde26f191cf1b2c7
Source dataset
uspto-grants-2009_01
Patent number
US07482452B2

Reaction notes

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