Tetrahydrofuran → HCID 87126738, compound

HRID 1698193Notes

Reaction equation

HRID 1698193 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[CH:5][N:4]=[CH:3]1.[CH3:9][C:10]([S@:13]([NH2:15])=[O:14])([CH3:12])[CH3:11].[CH2:16]1COC[CH2:17]1>CCOCC.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][N:2]1[C:6](/[C:7](=[N:15]/[S:13]([C:10]([CH3:12])([CH3:11])[CH3:9])=[O:14])/[CH2:16][CH3:17])=[CH:5][N:4]=[CH:3]1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 5735921-methyl-1H-imidazole-5-carbaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 87126738HCID 87126738, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-methyl-3H-imidazole-4-carbaldehyde (1.40 g, 12.7 mmol), (R)-(+)-2-methyl-2-propanesulfinamide (2.36 g, 19.1 mmol) and titanium (IV) isopropoxide (11.2 mL, 38.1 mmol) in THF (10 mL) was warmed at reflux for 18 hours. The mixture was cooled to room temperature, and diluted with ether (100 mL) and water (6 mL). The mixture was stirred for 10 minutes and then dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes, and concentrated to afford 2-methyl-propane-2-sulfinic acid [1-(3-methyl-3H-imidazol-4-yl)-prop-(E)-ylidene]-amide as a yellow solid.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 18 hours
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of 0-100% EtOAc in hexanes
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d614e9c5f7aa426ba4410d37c4e5dac6
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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