m-Tolyl isocyanate → HCID 14996927, compound

HRID 1769701Notes

Reaction equation

HRID 1769701 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([CH:12]([CH3:23])[C:13]([N:15]([CH3:22])[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].[CH3:24][C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1>>[CH3:22][N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13](=[O:14])[CH: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:32]([NH:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([CH3:24])[CH:26]=1)=[O:33])[CH3:23]

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 14996925HCID 14996925, compound

Product 1

HCID 14996927HCID 14996927, compoundYield 35.7%

Procedure

The procedure is analogous to that described in Example 1, but 1.0 g of (RS)-2-(2-amino-N-phenylacetamido)-N-methyl-N-phenylpropionamide and 0.42 g of 3-methylphenyl isocyanate are used as the starting material. After recrystallization from a mixture of acetonitrile and dimethylformamide (93-7 by volume), 0.5 g of (RS)-N-methyl-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}-N-phenylpropionamide melting at 214° C. is obtained.

Workup

  1. customAfter recrystallization
  2. additionfrom a mixture of acetonitrile and dimethylformamide (93-7 by volume)

Sources & evidence

ORD record
ord-fab235764ae740df9457445a41d08ba0
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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