m-Tolyl isocyanate → HCID 19001984, compound

HRID 2259962Notes

Reaction equation

HRID 2259962 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[O:4].[CH3:22][C:23]1[CH:24]=[C:25]([N:29]=[C:30]=[O:31])[CH:26]=[CH:27][CH:28]=1>>[CH3:13][O:12][C:8]1[CH:7]=[C:6]([N:5]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:3](=[O:4])[CH2:2][NH:1][C:30]([NH:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([CH3:22])[CH:24]=2)=[O:31])[CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19002040HCID 19002040, compound

Product 1

HCID 19001984HCID 19001984, compoundYield 65.9%

Procedure

The procedure used is similar to that described in Example 1, but starting with tert-butyl 2-[2-amino-N-(3-methoxyphenyl)acetamido]acetate (2.3 g) and 3-methylphenyl isocyanate (1.1 g). The product obtained is purified by chromatography on silica (0.04-0.063 mm) (150 g) contained in a column 3.5 cm in diameter [eluent: cyclohexane/ethyl acetate (70:30 by volume)], using an excess pressure of nitrogen of 40 kPa and collecting 20-cc fractions. Fractions 10 to 16 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallisation in diisopropyl ether, tert-butyl 2-{N-(3-methoxyphenyl)-2-[3-(3-methylphenyl)ureido]acetamido}acetate (2.2 g), m.p. approximately 60° C., is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on silica (0.04-0.063 mm) (150 g)
  3. customcollecting 20-cc fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallisation in diisopropyl ether

Sources & evidence

ORD record
ord-2df26cbfc9ca4cfc82ecf58255fa8d8f
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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