Hydrazine hydrate (1:1) → HCID 14996937, compound

HRID 1769705Notes

Reaction equation

HRID 1769705 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:33])[CH2:11][N:12]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:13](=[O:26])[CH2:14][N:15]2C(=O)C3=CC=CC=C3[C:16]2=[O:25])=[CH:5][CH:4]=1.O.NN.[CH3:37][C:38]1[CH:39]=[C:40]([N:44]=C=O)[CH:41]=[CH:42][CH:43]=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:33])[CH2:11][N:12]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:13](=[O:26])[CH2:14][NH:15][C:16]([NH:44][C:40]2[CH:41]=[CH:42][CH:43]=[C:38]([CH3:37])[CH:39]=2)=[O:25])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 69303m-Tolyl isocyanateHCID 14996935HCID 14996935, compound

Product 1

HCID 14996937HCID 14996937, compoundYield 9.9%

Procedure

The procedure is analogous to that described in Example 23, but 1.2 g of N-(4-methoxyphenyl)-2-(N-phenyl-2-phthalimidoacetamido)acetamide, 0.28 g of hydrazine hydrate and 0.38 g of 3-methylphenyl isocyanate are used as the starting material. The product obtained is purified by chromatography on 25 g of silica (0.065-0.200 mm) contained in a column 1.7 cm in diameter [eluent: methylene chloride/ethyl acetate (80-20 by volume)], collecting 25 cm3 fractions. Fractions 2 to 7 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from acetonitrile, 0.12 g of N-(4-methoxyphenyl)-2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetamide melting at 194° C. is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 25 g of silica (0.065-0.200 mm)
  3. customcollecting 25 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-3e730aa5b364473b98ed794803cd8c5b
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

Loading…