Thionyl Chloride → HCID 18951116, compound

HRID 1492511Notes

Reaction equation

HRID 1492511 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[NH:10][CH2:11][C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=1.[NH:16]([CH:23]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(Cl)(Cl)=O>>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[NH:10][CH2:11][C:12]([N:16]([CH:23]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 18951148HCID 18951148, compound

Product 1

HCID 18951116HCID 18951116, compoundYield 33.1%

Procedure

The procedure is as in Example 1, but 0.85 g of 2-[3-(3-methylphenyl)ureido]acetic acid, 1.25 g of di-tert-butyl 2-anilinomalonate and 0.3 cm3 of thionyl chloride are used as starting materials. The product obtained is purified by chromatography on 50 g of silica (0.04-0.063 mm) contained in a column 3 cm in diameter [eluent: methanol/dichloromethane (1.5/98.5 by volume)], using an excess pressure of 40 kPa of nitrogen and collecting 25-cm3 fractions. Fractions 6 to 15 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 35° C. and the residue obtained is crystallization from 10 cm3 of diethyl ether. 0.67 g of di-tert-butyl 2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}malonate melting at 175° C. are then obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 50 g of silica (0.04-0.063 mm)
  3. customcollecting 25-cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 35° C.
  5. customthe residue obtained
  6. customcrystallization from 10 cm3 of diethyl ether

Sources & evidence

ORD record
ord-2d159e6412fa4958b5de3bfd5baf643a
Source dataset
uspto-grants-1994_12
Patent number
US05374656

Reaction notes

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