1-Propanol → 5-Bromo-2',4-dihydroxy-3-n-propyloxycarbonylbenzanilide

HRID 2398280Notes

Reaction equation

HRID 2398280 reaction equation
[Br:1][C:2]1[C:3]([OH:21])=[C:4]([C:18]([OH:20])=[O:19])[CH:5]=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])=[O:8].S(=O)(=O)(O)O.[OH-].[Na+].[CH2:29](O)[CH2:30][CH3:31]>>[Br:1][C:2]1[C:3]([OH:21])=[C:4]([C:18]([O:20][CH2:29][CH2:30][CH3:31])=[O:19])[CH:5]=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])=[O:8]

Participants

5

Reactant 4

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 20327542HCID 20327542, compound

Product 1

HCID 203275405-Bromo-2',4-dihydroxy-3-n-propyloxycarbonylbenzanilideYield 54.5%

Procedure

5-Bromo-3-carboxy-2',4-dihydroxybenzanilide (1.0 g.) described in Example 4 was dissolved in n-propanol (50 ml.), and after adding conc. sulfuric acid (1 ml.) the solution was refluxed for 8 hours. After neutralizing with sodium hydroxide solution, the reaction solution was evaporated to dryness and the residue was washed with 5% sodium bicarbonate solution and recrystallized from aqueous acetone to give 5-bromo-2',4-dihydroxy-3-n-propyloxycarbonylbenzanilide (0.61 g.). Yield: 54.5% Melting point 198°-200° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customthe reaction solution was evaporated to dryness
  3. washthe residue was washed with 5% sodium bicarbonate solution
  4. customrecrystallized from aqueous acetone

Sources & evidence

ORD record
ord-84cae6c07a84462ab49fef8c1ba21f62
Source dataset
uspto-grants-1977_05
Patent number
US04024253

Reaction notes

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