Imidazole → HCID 22622957, compound

HRID 840382Notes

Reaction equation

HRID 840382 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([CH2:13]Cl)[CH:11]=[CH:12][C:4]=2[O:3]1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>CS(C)=O>[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([CH2:13][N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 22623180HCID 22623180, compound

Product 1

HCID 22622957HCID 22622957, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

1.25 g (5.9 mmol) of (±)-2-methyl-3-oxo-6-chloromethyl-3,4-dihydro-2H-1,4-benzoxazine is dissolved in 12.5 ml of dimethyl sulfoxide, mixed with 0.804 g (11.8 mmol) of imidazole and stirred for 8 hours at 70° C. After stirring overnight at room temperature, the reaction mixture is spun on an oil pump until dry, and the residue is chromatographed on silica gel (mobile solvent: methylene chloride/ethanol). 940 mg (65.7%) of the desired imidazole compound is obtained, melting point 219-222° C.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. customuntil dry
  3. customthe residue is chromatographed on silica gel (mobile solvent: methylene chloride/ethanol)

Sources & evidence

ORD record
ord-37322657d8ed45f0a129ebe53573f182
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

Loading…