Thionyl Chloride → HCID 18951155, compound

HRID 1492498Notes

Reaction equation

HRID 1492498 reaction equation
[NH:1]([CH2:8][C:9]([O:11][C:12]1([CH3:18])[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.[CH3:19][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][C:12]2([CH3:18])[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:31])[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 18951147HCID 18951147, compound

Product 1

HCID 18951155HCID 18951155, compoundYield 11.4%

Procedure

The procedure is carried out in a manner analogous to that described in Example 1, but using 3.0 g of 1-methylcyclohexyl 2-anilinoacetate, 2.5 g of 2-[3-(3-methylphenyl)ureido]acetic acid and 0.9 cm3 of thionyl chloride as starting materials. The product obtained is purified by chromatography on 40 g of silica (0.063-0.200 mm) contained in a column 1.5 cm in diameter [eluent: cyclohexane/ethyl acetate (70/30 by volume)], collecting 20-cm3 fractions. Fractions 3 to 8 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After-recrystallization from an acetonitrile/diisopropyl ether mixture (50/50 by volume), 0.6 g of 1-methylcyclohexyl 2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetate melting at 192° C. is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 40 g of silica (0.063-0.200 mm)
  3. customcollecting 20-cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter-recrystallization from an acetonitrile/diisopropyl ether mixture (50/50 by volume)

Sources & evidence

ORD record
ord-62f5224bde73465db04e614e1060ccd5
Source dataset
uspto-grants-1994_12
Patent number
US05374656

Reaction notes

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