Acetonitrile → HCID 18930606, compound

HRID 1598897Notes

Reaction equation

HRID 1598897 reaction equation
S(Cl)(Cl)=[O:2].[CH2:5]([O:12]NC(=C=O)C(O)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:20][C:21]1[CH:34]=[CH:33][CH:32]=[CH:31][C:22]=1[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].[C:35](=O)([O-])[OH:36].[Na+].[C:40](#[N:42])[CH3:41]>>[CH2:5]([O:12][C:35]([NH:42][CH2:40][C:41]([NH:20][C:21]1[CH:34]=[CH:33][CH:32]=[CH:31][C:22]=1[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24])=[O:2])=[O:36])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 24386Thionyl ChlorideHCID 760802-AminobenzophenoneHCID 516892Sodium BicarbonateHCID 86752397HCID 86752397, compound

Product 1

HCID 18930606HCID 18930606, compoundYield 97.3%

Procedure

Thionyl chloride (4 ml, 55 mmol) is added dropwise to a solution of N-benzyloxy-carbonylglycine (12.6 g, 60 mmol) in hexamethylphosphonyltriamide (70 ml) and acetonitrile (20 ml) under stirring at -4°-5° C., and the stirring at -5° C. is continned for another 10 minutes. 2-Aminobenzophenone (9.86 g, 50 mmol) is added to the reaction mixture in five portions, and the mixture is stirred at room temperature for 3 hours. The reaction mixture is neutralized with a saturated aqueous solution of sodium hydrogencarbonate, and extracted with ethyl acetate. The organic phase is washed with water, dried (magnesium sulfate) and then concentrated under reduced pressure. The resultant raw product is recrystallized from hexane to obtain the title compound 2a (18.89 g, 97.3%).

Workup

  1. stirringthe mixture is stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant raw product is recrystallized from hexane

Sources & evidence

ORD record
ord-9b2203e8f7314aa2a888005742106573
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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