m-Tolyl isocyanate → HCID 14996848, compound

HRID 1769690Notes

Reaction equation

HRID 1769690 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]([Cl: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>>[Cl: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 14996847HCID 14996847, compound

Product 1

HCID 14996848HCID 14996848, compoundYield 32.9%

Procedure

The procedure is analogous to that described in Example 1, but 2.2 g of 2-(2-amino-N-phenylacetamido)-N-(4-chlorophenyl)-N-methylacetamide and 0.87 g of 3-methylphenyl isocyanate are used as the starting material. The product obtained is purified by chromatography on 60 g of silica (0.065-0.200 mm) contained in a column 2.5 cm in diameter [eluent: methylene chloride/methanol (99-1 by volume)], collecting 20 cm3 fractions. Fractions 30 to 43 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from acetonitrile, 1.0 g of N-(4-chlorophenyl)-N-methyl-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetamide melting at 160° C. is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 60 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 acetonitrile

Sources & evidence

ORD record
ord-fa68c1fac3704caeb6b39632643d40bb
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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