Acetic Acid → HCID 13371117, compound

HRID 1154359Notes

Reaction equation

HRID 1154359 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:9][CH2:10][NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+].C(O)(=O)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[CH:9][CH2:10][NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 20435418HCID 20435418, compound

Product 1

HCID 13371117HCID 13371117, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 1.3 g. of p-[[3,3-bis(p-chlorophenyl)allyl]amino]benzoic acid, ethyl ester, 40 ml. of ethanol, and 4.6 ml. of 1N sodium hydroxide is heated at reflux for 28 hours, cooled, and then diluted with an equal volume of water. A 0.26 ml. portion of glacial acetic acid is added, and the mixture is cooled in ice. The solid is collected, washed with water, and recrystallized from absolute ethanol, giving 600 mg. of the desired product, m.p. 231°-235° C.

Workup

  1. additionA suspension of 1.3 g
  2. temperatureat reflux for 28 hours
  3. temperaturecooled
  4. temperaturethe mixture is cooled in ice
  5. customThe solid is collected
  6. washwashed with water
  7. customrecrystallized from absolute ethanol
  8. customgiving 600 mg

Sources & evidence

ORD record
ord-1f9bf407cbb7483894b7305adce29414
Source dataset
uspto-grants-1984_12
Patent number
US04489094

Reaction notes

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