Ethanol → HCID 68456487, compound

HRID 2358852Notes

Reaction equation

HRID 2358852 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+:10].[CH:11]1([N:14]=[C:15]=[S:16])[CH2:13][CH2:12]1.[C:17](#[N:19])[CH3:18].[CH3:20][CH2:21][OH:22]>C1COCC1>[C:17]([C:18]1[CH:1]=[CH:20][C:21](=[O:22])[N:14]([CH:11]2[CH2:13][CH2:12]2)[C:15]=1[S-:16])#[N:19].[Na+:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 6342AcetonitrileHCID 92463Cyclopropyl isothiocyanateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 68456487HCID 68456487, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium bis(trimethylsilyl)amide (122 mL of a 1.0M solution in THF, 122 mmol) was added to a solution of cyclopropyl isothiocyanate (4.85 g, 48.9 mmol) and acetonitrile (25.5 mL, 10 eq) in THF (50 mL) at −78° C. The mixture was allowed to warm to r.t. over 2 h. N,N-Dimethyluracil (5.9 g, 49 mmol) and EtOH (60 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 taken up in a mixture of EtOH and EtOAc then Et2O was added. The sticky solid was filtered off and dried to give the title compound (11 g, crude) which was used 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. additionThe residue was taken up in a mixture of EtOH and EtOAc
  5. additionEt2O was added
  6. filtrationThe sticky solid was filtered off
  7. customdried

Sources & evidence

ORD record
ord-e860ec182ad84ac5a5363b7d9933b4c6
Source dataset
uspto-grants-2010_07
Patent number
US07763729B2

Reaction notes

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