Imidazole → HCID 18930613, compound

HRID 1598906Notes

Reaction equation

HRID 1598906 reaction equation
P(Cl)(Cl)(Cl)=O.N1C=CN=C1.[CH2:11]([O:18][C:19]([NH:21][CH2:22][C:23]([OH:25])=O)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29].C(=O)([O-])O.[Na+]>CC(N(C)C)=O.C(OCC)(=O)C.O>[I:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH:29][C:23](=[O:25])[CH2:22][NH:21][C:19]([O:18][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:20]

Participants

9

Reactant 5

HCID 795ImidazoleHCID 119952-IodoanilineHCID 14349BenzyloxycarbonylglycineHCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 18930613HCID 18930613, compoundYield 86.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Procedure

Phosphorus oxychloride (2.2 ml, 24 mmol), imidazole (2.7 g, 40 mmol), and N-benzyloxycarbonylglycine (5.0 g, 24 mmol) are added to dimethylacetamide (32 ml) under ice cooling and stirring. After stirring for 5 minutes, a solution of 2-iodoaniline (4.4 g, 20 mmol) in DMA (10 ml) is added dropwise. The reaction mixture is stirred at 50° C. for 3 hours. After allowing to cool, water and ethyl acetate are added to the reaction mixture, and a saturated aqueous solution of sodium hydrogencarbonate is added to make pH 9, and the aqueous phase is extracted twice with ethyl acetate. The organic layer is washed with a saturated saline, dried over anhydrous magnesium sulfate, and then concentrated. To the residue is added isopropylether (40 ml), and the precipitated solid is filtered off to obtain the objective compound (7.10 g). Yield 86%.

Workup

  1. stirringAfter stirring for 5 minutes
  2. stirringThe reaction mixture is stirred at 50° C. for 3 hours
  3. temperatureto cool
  4. extractionthe aqueous phase is extracted twice with ethyl acetate
  5. washThe organic layer is washed with a saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. additionTo the residue is added isopropylether (40 ml)
  9. filtrationthe precipitated solid is filtered off

Sources & evidence

ORD record
ord-ad4e993a0ed74487bf1b548eefb9c186
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

Loading…