Dimethyl Sulfoxide → HCID 86750039, compound

HRID 1079296Notes

Reaction equation

HRID 1079296 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]([NH2:14])=[O:13])([O-:3])=[O:2].CS(C)=O.C(N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.CO.CC(O)=O>[C:26]([NH:14][C:12](=[O:13])[CH2:11][NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22447459HCID 22447459, compound

Product 1

HCID 86750039HCID 86750039, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21877243DCM MeOH AcOHSolvent

Procedure

2-Nitrophenylglycine amide, 1 DMSO (500 mg, 1.83 mmol) was suspended in chloroform (20 ml) and triethylamine (390 μl, 2.80 mmol) was added. Subsequently benzoyl chloride (330 μl, 2.8 mmol) was added with stirring. The reaction was followed by TLC using as eluent: CH2Cl2 /MeOH/AcOH (85:10:5) and after 1 h at 20° C. the reaction mixture was treated with a saturated solution of NaHCO3, dried over anhydrous MgSO4 and evaporated to dryness. The product was recrystallized from absolute ethanol. Yield: 600 mg (77%); mp 178°-180° C., identified by 1H NMR spectroscopy. ##STR13##

Workup

  1. dry with materialdried over anhydrous MgSO4
  2. customevaporated to dryness
  3. customThe product was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-741c454611c9440fb68c5158700b8fa1
Source dataset
uspto-grants-1996_12
Patent number
US05580751

Reaction notes

Loading…