Thionyl Chloride → HCID 14996964, compound

HRID 1769707Notes

Reaction equation

HRID 1769707 reaction equation
[C:1]1([NH:7][CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:36])[NH:31][CH2:32][C:33](O)=[O:34])[CH:26]=[CH:27][CH:28]=1.S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>ClCCCl.C(Cl)Cl>[CH3:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:36])[NH:31][CH2:32][C:33]([N:7]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9](=[O:10])[N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:34])[CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 14996962HCID 14996962, compound

Product 1

HCID 14996964HCID 14996964, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 1.6 g of (RS)-1-(α-phenylaminophenylacetyl)pyrrolidine and 1.2 g of 2-[3-(3-methylphenyl)ureido]acetic acid in 50 cm3 of anhydrous 1,2-dichlorethane is heated to reflux. 0.68 g of thionyl chloride is added, maintaining reflux until the evolution of gas has ceased. The reaction mixture is then poured into 30 cm3 of a saturated aqueous sodium bicarbonate solution and 50 cm3 of methylene chloride are then added. The organic phase is washed with 50 cm3 of distilled water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The product obtained is purified by chromatography on 50 g of silica (0.065-0.200 mm) contained in a column 2.2 cm in diameter [eluent: ethyl acetate/methylene chloride (50-50 by volume)], collecting 25 cm3 fractions. Fractions 9 to 22 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from a mixture of ethyl acetate and acetonitrile (90-10 by volume), 0.55 g of (RS)-2-[3-(3-methylphenyl)ureido]-N-[2-oxo-1-phenyl-2-(1-pyrrolidinyl)ethyl]-N-phenylacetamide melting at 138° C. is obtained.

Workup

  1. temperatureis heated to reflux
  2. temperaturemaintaining
  3. temperaturereflux until the evolution of gas
  4. additionare then added
  5. washThe organic phase is washed with 50 cm3 of distilled water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  8. customThe product obtained
  9. customis purified by chromatography on 50 g of silica (0.065-0.200 mm)
  10. customcollecting 25 cm3 fractions
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  12. customAfter recrystallization
  13. additionfrom a mixture of ethyl acetate and acetonitrile (90-10 by volume)

Sources & evidence

ORD record
ord-376888b22dc142d7ace81da5926f6176
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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