Thionyl Chloride → HCID 19754792, compound

HRID 1588860Notes

Reaction equation

HRID 1588860 reaction equation
[NH:1]([CH2:8][C:9]([O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:32])[NH:27][CH2:28][C:29](O)=[O:30])[CH:22]=[CH:23][CH:24]=1.S(Cl)(Cl)=O>>[CH3:18][C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:32])[NH:27][CH2:28][C:29]([N:1]([CH2:8][C:9]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:10])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:30])[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 19754770HCID 19754770, compound

Product 1

HCID 19754792HCID 19754792, compoundYield 14.7%

Procedure

The procedure is similar to that described in Example 28, but starting with cyclohexyl 2-anilinoacetate (8.6 g), 2-[3-(3-methylphenyl)ureido]acetic acid (7.7 g) and thionyl chloride (2.7 cc). The product obtained is purified by chromatography on silica gel (0.063-0.200 mm; 150 g) contained in a column 3.5 cm in diameter [eluant: methylene chloride/methanol (99:1 by volume)], collecting 20-cc fractions. Fractions 6 to 18 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in isopropanol, cyclohexyl 2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetate (2.3 g), m.p. 176° C., is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on silica gel (0.063-0.200 mm; 150 g)
  3. customcollecting 20-cc fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallization in isopropanol

Sources & evidence

ORD record
ord-a350ac2849714e72bc9f7b80b25b0cc7
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

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