Hydrazine hydrate (1:1) → HCID 14996908, compound

HRID 1769706Notes

Reaction equation

HRID 1769706 reaction equation
[CH2:1]([N:3]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:4](=[O:27])[CH2:5][N:6]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:7](=[O:20])[CH2:8][N:9]1C(=O)C2=CC=CC=C2[C:10]1=[O:19])[CH3:2].O.NN.[CH3:37][C:38]1[CH:39]=[C:40]([N:44]=C=O)[CH:41]=[CH:42][CH:43]=1>>[CH2:1]([N:3]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:4](=[O:27])[CH2:5][N:6]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:7](=[O:20])[CH2:8][NH:9][C:10]([NH:44][C:40]1[CH:41]=[CH:42][CH:43]=[C:38]([CH3:37])[CH:39]=1)=[O:19])[CH3:2]

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 69303m-Tolyl isocyanateHCID 14996906HCID 14996906, compound

Product 1

HCID 14996908HCID 14996908, compoundYield 30.5%

Procedure

The procedure is analogous to that described in Example 23, but 3.1 g of N-ethyl-N-phenyl-2-(N-phenyl-2-phthalimidoacetamido)acetamide, 0.4 g of hydrazine hydrate and 0.54 g of 3-methylphenyl isocyanate are used as the starting material. The product obtained is purified by chromatography on 20 g of silica (0.065-0.200 mm) contained in a column 1.7 cm in diameter [eluent: methylene chloride], collecting 20 cm3 fractions. Fractions 10 to 23 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from diethyl ether, 0.55 g of N-ethyl-N-phenyl-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetamide melting at 158° C. is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 20 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 diethyl ether

Sources & evidence

ORD record
ord-40cbb69a55aa4989b89cc91c23f0e110
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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