Water → HCID 178427881, compound

HRID 27179Notes

Reaction equation

HRID 27179 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:18]([CH3:19])=[C:17]([CH:20]2[S:25][CH2:24][C:23](=[N:26]O)[CH2:22][S:21]2)[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]1[C:18]([CH3:19])=[C:17]([C@H:20]2[S:25][CH2:24][C@H:23]([NH2:26])[CH2:22][S:21]2)[N:16]=[CH:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 233436822-(1-Benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one oxime

Product 1

HCID 178427881HCID 178427881, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of lithium aluminum hydride (2.9 g., 0.076 mole) in dry tetrahydrofuran (120 ml.) under a nitrogen atmosphere is added dropwise a solution of 2-(1-benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one oxime (21.3 g., 0.0668 mole) in dry tetrahydrofuran (130 ml.). After heating at 70° C. for one hour, water (40 ml.) is added cautiously and the mixture is filtered hot. The solvent is evaporated and the residue is chased with ethanol to remove traces of water to give a viscous oil (17.0 g.). Careful chromatography on silica gel by gradient elution with 2-6% methanol/chloroform affords 2.2 g. of the trans isomer and 7.3 g. of the cis isomer as viscous semi-solids.

Workup

  1. filtrationthe mixture is filtered hot
  2. customThe solvent is evaporated
  3. customto remove traces of water
  4. customto give a viscous oil (17.0 g.)
  5. washCareful chromatography on silica gel by gradient elution with 2-6% methanol/chloroform
  6. customaffords 2.2 g

Sources & evidence

ORD record
ord-434b12caf1be4b3aaf88d23985c77467
Source dataset
uspto-grants-1980_09
Patent number
US04220654

Reaction notes

Loading…