Water → HCID 22621193, compound

HRID 841162Notes

Reaction equation

HRID 841162 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:9]=[N:10][O:11][C:12]=2[CH:13]2[CH2:15][CH2:14]2)=[O:7])=[C:4]([N:18]([CH3:23])S(C)(=O)=O)[C:3]=1[O:24][CH2:25][CH3:26].S(=O)(=O)(O)O.O.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:9]=[N:10][O:11][C:12]=2[CH:13]2[CH2:15][CH2:14]2)=[O:7])=[C:4]([NH:18][CH3:23])[C:3]=1[O:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 22621105HCID 22621105, compound

Product 1

HCID 22621193HCID 22621193, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-[4-bromo-3-ethoxy-2-(N-methyl-N-methylsulphonylamino)benzoyl]-5-cyclopropylisoxazole (0.5 g) and concentrated sulphuric acid (6 ml) in acetic acid (9 ml) was heated at 70° C. for 4 hours, then at 90° C. for 4 hours. The mixture was poured into excess water and carefully brought to pH 5.5 by the addition of 2M sodium hydroxide solution. extracted with ethyl acetate, dried (anhydrous magnesium sulphate), evaporated and purified by column chromatography to yield 4-[4-bromo-3-ethoxy-2-(methylamino)benzoyl]-5-cyclopropylisoxazole (0.096 g), NMR 1.15(m,2H), 1.25(m,2H), 1.4(t,3H), 2.5(m,1H), 2.9(s,3H), 3.9(q,2H), 6.8(d,1H), 7.05(d,1H), 7.1(s,1H), 8.25(s,1H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (anhydrous magnesium sulphate)
  3. customevaporated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-60522615152043b8a46638c9cb525259
Source dataset
uspto-grants-2002_04
Patent number
US06369270B1

Reaction notes

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