Acetic Acid → HCID 22621067, compound

HRID 610755Notes

Reaction equation

HRID 610755 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, 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. temperaturewith cooling
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-0c51fe93ad11408081ec187608bc742c
Source dataset
uspto-grants-1999_12
Patent number
US05998653

Reaction notes

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