Sodium Carbonate → HCID 14801578, compound

HRID 483932Notes

Reaction equation

HRID 483932 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:50])[N:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH:43]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)[C:30]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([O:39]C(=O)C)=[CH:35][CH:34]=3)=[O:31])[CH:23]=2)[CH:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH:14]1([N:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH:43]3[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]3)[C:30]([NH:32][C:33]3[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=3)=[O:31])[CH:23]=2)[C:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=2)=[O:50])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 14801553HCID 14801553, compound

Product 1

HCID 14801578HCID 14801578, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2 g 1,3-bis[[3-(p-acetoxyphenyl)-1-cycloheptylureido]methyl]benzene (compound of Example 42), 30 ml ethanol and 30 ml of 5% aqueous sodium carbonate solution was heated under reflux for ten minutes. After distilling off the ethanol under reduced pressure, water was added to the residue, and the resulting mixture was acidified by addition of concentrated hydrochloric acid under ice cooling. The solid which separated out was collected by filtration and recrystallized from methanol, giving 1 g of 1,3-bis[[1-cycloheptyl-3-(p-hydroxyphenyl)ureido]methyl]benzene.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for ten minutes
  3. distillationAfter distilling off the ethanol under reduced pressure, water
  4. additionwas added to the residue
  5. additionthe resulting mixture was acidified by addition of concentrated hydrochloric acid under ice cooling
  6. customThe solid which separated out
  7. filtrationwas collected by filtration
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7242101a65ab4e77ad788db4cbe10919
Source dataset
uspto-grants-1993_07
Patent number
US05227492

Reaction notes

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