m-Tolyl isocyanate → HCID 20097139, compound

HRID 1769719Notes

Reaction equation

HRID 1769719 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13]([N:15]([CH:22]([CH3:24])[CH3:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1>>[CH:22]([N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](=[O:14])[CH2:12][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](=[O:4])[CH2:2][NH:1][C:33]([NH:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([CH3:25])[CH:27]=1)=[O:34])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 20097155HCID 20097155, compound

Product 1

HCID 20097139HCID 20097139, compoundYield 36.3%

Procedure

The procedure is analogous to that described in Example 81, but 0.6 g of 2-(2-amino-N-phenylacetamido)-N-isopropyl-N-phenylacetamide and 0.24 g of 3-methylphenyl isocyanate are used as the starting material. The crude product obtained is purified by chromatography on 30 g of silica (0.065-0.200 mm) contained in a column 1.5 cm in diameter [eluent: dichloromethane/ethyl acetate (80/20 by volume)], collecting 20 cm3 fractions. Fractions 6 to 10 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from diethyl ether, 0.3 g of N-isopropyl 2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}-N-phenylacetamide melting at 170° C is obtained.

Workup

  1. customThe crude product obtained
  2. customis purified by chromatography on 30 g of silica (0.065-0.200 mm)
  3. customcollecting 20 cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallization from diethyl ether

Sources & evidence

ORD record
ord-2f52086a45054fecbeafb22599fcc7c0
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

Loading…