Thionyl Chloride → HCID 19754786, compound

HRID 1588859Notes

Reaction equation

HRID 1588859 reaction equation
[NH:1]([CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:33])[NH:28][CH2:29][C:30](O)=[O:31])[CH:23]=[CH:24][CH:25]=1.S(Cl)(Cl)=O>>[CH3:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:33])[NH:28][CH2:29][C:30]([N:1]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:31])[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 21693963HCID 21693963, compound

Product 1

HCID 19754786HCID 19754786, compoundYield 21.8%

Procedure

The procedure is similar to that described in Example 28, but starting with benzyl 2-anilinoacetate (3.6 g), 2-[3-(3-methylphenyl)ureido]acetic acid (3.1 g) and thionyl chloride (1.65 g). The product obtained is purified by chromatography on silica gel (0.063-0.200 mm; 60 g) contained in a column 2 cm in diameter [eluant: cyclohexane/ethyl acetate (50:50 by volume)], collecting 20-cc fractions. Fractions 5 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in acetonitrile, benzyl 2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetate (1.4 g), m.p. 140° C., is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on silica gel (0.063-0.200 mm; 60 g)
  3. customcollecting 20-cc fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-e1913e825f43461ca032a34b7d03891e
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

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