m-Tolyl isocyanate → HCID 20097198, compound

HRID 1769711Notes

Reaction equation

HRID 1769711 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13]([N:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH3:16])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:24][C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1>>[F:23][C:20]1[CH:19]=[CH:18][C:17]([N:15]([CH3:16])[C:13](=[O:14])[CH2:12][N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3](=[O:4])[CH2:2][NH:1][C:32]([NH:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH3:24])[CH:26]=2)=[O:33])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 20097051HCID 20097051, compound

Product 1

HCID 20097198HCID 20097198, compoundYield 48.7%

Procedure

The procedure is analogous to that described in Example 1, but 2.6 g of 2-(2-amino-N-phenylacetamido)-N-(4-fluorophenyl)-N-methylacetamide and 1.1 g of 3-methylphenyl isocyanate are used as the starting material. The crude product obtained is purified by chromatography on 60 g of silica (0.065-0.200 mm) contained in a column 2.0 cm in diameter [eluent: ethyl acetate/cyclohexane (50-50 by volume)], collecting 30 cm3 fractions. Fractions 6 to 10 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from ethyl acetate, 1.8 g of N-(4-fluorophenyl)-N-methyl-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetamide melting at 135° C is obtained.

Workup

  1. customThe crude product obtained
  2. customis purified by chromatography on 60 g of silica (0.065-0.200 mm)
  3. customcollecting 30 cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-8741a91b57104d8192398412a630dac3
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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