Ethanol → HCID 67532402, compound

HRID 2358851Notes

Reaction equation

HRID 2358851 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+:10].[C:11]1([CH3:20])[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[S:19])=[CH:13][CH:12]=1.[CH3:21][CH2:22][OH:23]>C1COCC1.C(#N)C>[C:14]([C:13]1[CH:12]=[CH:21][C:22](=[O:23])[N:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:20])=[CH:12][CH:13]=2)[C:18]=1[S-:19])#[N:17].[Na+:10]

Participants

6

Reactant 3

HCID 702EthanolHCID 12149p-Tolyl isothiocyanateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 67532402HCID 67532402, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium bis(trimethylsilyl)amide (36.8 mL, 1.0M in THF, 36.8 mmol) was added slowly to a solution of 4-tolyl isothiocyanate (2.5 g, 16.75 mmol) in THF (30 mL) and acetonitrile (5 mL) at −78° C. The mixture was warmed to r.t. over 1 h. N,N-Dimethyluracil (2.35 g, 16.75 mmol) and EtOH (20 mL) were added and the mixture heated at reflux for 4 h. Volatiles were removed in vacuo and the residue was dissolved in EtOH (6 mL). Et2O (˜60 mL) was added slowly to produce a fine, off-white solid. The suspension was cooled to 0° C. and the solid filtered off, washed with Et2O and dried to give the title compound as an off-white solid (1.7 g, 39%). δH (DMSO-d6) 7.15-7.12 (3H, m), 6.80-6.77 (2H, m), 5.60 (1H, d, J 9.1 Hz), 2.30 (3H, s).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 h
  3. customVolatiles were removed in vacuo
  4. dissolutionthe residue was dissolved in EtOH (6 mL)
  5. additionEt2O (˜60 mL) was added slowly
  6. customto produce a fine, off-white solid
  7. temperatureThe suspension was cooled to 0° C.
  8. filtrationthe solid filtered off
  9. washwashed with Et2O
  10. customdried

Sources & evidence

ORD record
ord-c9bc47fafc8c4aeebda7f6be9801ba9e
Source dataset
uspto-grants-2010_07
Patent number
US07763729B2

Reaction notes

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