Thionyl Chloride → HCID 19002047, compound

HRID 2259961Notes

Reaction equation

HRID 2259961 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:31])[NH:26][CH2:27][C:28](O)=[O:29])[CH:21]=[CH:22][CH:23]=1.S(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:28](=[O:29])[CH2:27][NH:26][C:25]([NH:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([CH3:17])[CH:19]=2)=[O:31])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 19001987N-(4-Chlorophenyl)glycine 1,1-dimethylethyl ester

Product 1

HCID 19002047HCID 19002047, compoundYield 15.5%

Procedure

The procedure used is similar to that described in Example 17, but starting with tert-butyl 2-[(4-chlorophenyl)amino]acetate (1.8 g), 2-[3-(3-methylphenyl)-ureido]acetic acid (1.56 g) and thionyl chloride (0.89 g). The product obtained is purified by chromatography on silica (0.04-0.063 mm) (60 g) contained in a column 2.5 cm in diameter [eluent: cyclohexane/ethyl acetate (80:20 by volume)], using an excess pressure of nitrogen of 40 kPa and collecting 20-cc fractions. Fractions 21 to 25 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After crystallisation in acetonitrile, tert-butyl 2-{N-(4-chlorophenyl)-2-[3-(3-methylphenyl)ureido]acetamido}acetate (0.5 g), m.p. 125° C., is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on silica (0.04-0.063 mm) (60 g)
  3. customcollecting 20-cc fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter crystallisation in acetonitrile

Sources & evidence

ORD record
ord-c31188f070e045859e86fb5e5c645c3f
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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