Tetrahydrofuran → HCID 19825152, compound

HRID 727822Notes

Reaction equation

HRID 727822 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9](C2C=CC=CC=2)[N:8]=[C:7]1[CH:17]=[N:18]O)(=O)=O.[H-].[Na+].Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(O[CH2:33][CH3:34])(=O)C.O1[CH2:39][CH2:38][CH2:37][CH2:36]1>>[C:17]([CH:7]1[N:6]([C:34]2[CH:33]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:10]=[CH:9][N:8]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])#[N:18]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 136341188HCID 136341188, compound

Product 1

HCID 19825152HCID 19825152, compound

Procedure

1-(dimethylsulphamoyl)-2-(hydroxyiminomethyl)-4-phenylimidazole, m.p 165°-170° (dec.). A slurry of this product (0.882 g) in dry tetrahydrofuran (20 ml) was added to sodium hydride (90 mg of 80g suspension in oil) in dry tetrahydrofuran. After 1.5 hours at room temperature ethyl chloroformate (0.285 ml) was added and the mixture stirred overnight. The mixture was then added to ethyl acetate and worked up in conventional manner to give a viscous oil. This was purified by flash column chromatography to give 2-cyano-1-ethoxycarbonyl-3-phenylimidazole, m.p. 109°-111°. (Compound 3)

Workup

  1. customto give a viscous oil
  2. customThis was purified by flash column chromatography

Sources & evidence

ORD record
ord-e4378b2e678043359ee6a5272d3a1ed0
Source dataset
uspto-grants-1991_09
Patent number
US05045557

Reaction notes

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