Acetic Acid → HCID 22621067, compound

HRID 841165Notes

Reaction equation

HRID 841165 reaction equation
S(=O)(=O)(O)O.C(O)(=O)C.[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([N:20]([CH2:25][CH3:26])S(C)(=O)=O)[C:12]=1[O:27][CH2:28][CH3:29].[OH-].[Na+]>O>[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:20][CH2:25][CH3:26])[C:12]=1[O:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22620973HCID 22620973, compound

Product 1

HCID 22621067HCID 22621067, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of concentrated sulphuric acid (128 ml) and acetic acid (192 ml) was added with stirring to 4-bromo-3-ethoxy-2-(N-ethyl-N-methylsulphonylamino)benzoic acid (8.8 g) at 85° C. for 100 minutes and left to stand at ambient temperature for 3 days. After pouring onto excess water, the mixture was made neutral by the careful addition of sodium hydroxide solution with cooling&g, extracted with ethyl acetate, dried (anhydrous magnesium sulphate) and the solvent evaporated to give 4-bromo-2-ethylamino-3-ethoxybenzoic acid (4.74 g) as a brown solid, m.p. 129-139° C.

Workup

  1. additionwas added
  2. waitleft
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-bdf9ac697c5c4bee9a38a94f4f055b62
Source dataset
uspto-grants-2002_04
Patent number
US06369270B1

Reaction notes

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