m-Tolyl isocyanate → HCID 14996851, compound

HRID 1769691Notes

Reaction equation

HRID 1769691 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][C:18]=1[F:24])[CH3:16])=[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>>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[N:15]([CH3:16])[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]

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 14996850HCID 14996850, compound

Product 1

HCID 14996851HCID 14996851, compoundYield 37.2%

Procedure

The procedure is analogous to that described in Example 1, but 1.2 g of 2-(2-amino-N-phenyl-acetamido)-N-(2,4-difluorophenyl)-N-methylacetamide and 0.46 g of 3-methylphenyl isocyanate are used as the starting material. The product obtained is purified by chromatography on 70 g of silica (0.065-0.200 mm) contained in a column 2.5 cm in diameter [eluent: dichloromethane/methanol (99-1 by volume)], collecting 15 cm3 fractions. Fractions 24 to 36 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from diisopropyl ether, 0.6 g of N-(2,4-difluorophenyl)-N-methyl-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetamide melting at 100° C. is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 70 g of silica (0.065-0.200 mm)
  3. customcollecting 15 cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-cefb96229068467b9fb14773056e45c1
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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