Hydrazine hydrate (1:1) → HCID 14996902, compound

HRID 1769703Notes

Reaction equation

HRID 1769703 reaction equation
[CH3:1][N:2]([C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)[C:3](=[O:26])[CH2:4][N:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6](=[O:19])[CH2:7][N:8]1C(=O)C2=CC=CC=C2C1=O.O.NN.[CH3:37][C:38]1[CH:39]=[C:40]([N:44]=[C:45]=[O:46])[CH:41]=[CH:42][CH:43]=1>>[CH3:1][N:2]([C:27]1[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=1)[C:3](=[O:26])[CH2:4][N:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6](=[O:19])[CH2:7][NH:8][C:45]([NH:44][C:40]1[CH:41]=[CH:42][CH:43]=[C:38]([CH3:37])[CH:39]=1)=[O:46]

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 69303m-Tolyl isocyanateHCID 14996900HCID 14996900, compound

Product 1

HCID 14996902HCID 14996902, compoundYield 69.9%

Procedure

The procedure is analogous to that described in Example 23, but 1.6 g of N-methyl-N-(4-methylphenyl)-2-(N-phenyl-2-phthalimidoacetamido)acetamide, 0.36 g of hydrazine hydrate and 0.3 g of 3-methylphenyl isocyanate are used as the starting material. The product obtained is purified by chromatography on 80 g of silica gel (0.065-0.200 mm) contained in a column 2.5 cm in diameter [eluent: methylene chloride], collecting 20 cm3 fractions. Fractions 10 to 12 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from a mixture of ethyl acetate and diethyl ether (40-60 by volume), 0.7 g of N-methyl-N-(4-methylphenyl)-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetamide melting at 162° C. is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 80 g of silica gel (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
  6. additionfrom a mixture of ethyl acetate and diethyl ether (40-60 by volume)

Sources & evidence

ORD record
ord-15ef37e9e5484cb0ac62b04c8a6c4d51
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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