Bromoacetic Acid → HCID 57473751, compound

HRID 2247343Notes

Reaction equation

HRID 2247343 reaction equation
C([NH:4][C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=O)C.S([O-])([O-])=O.[Na+].[Na+].[C:27](=O)([O-])O.[Na+].BrCC(O)=O.[OH-].[Na+]>O1CCOCC1.O>[CH3:27][S:17]([C:14]1[CH:15]=[CH:16][C:11]([C:7]2[S:6][C:5]([NH2:4])=[N:9][C:8]=2[CH3:10])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

8

Reactant 5

HCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 85861720HCID 85861720, compound

Product 1

HCID 57473751HCID 57473751, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
91 °C

Procedure

4-(2-Acetylamino-4-methyl-thiazol-5-yl)-benzenesulfonyl chloride (Example 3a) (0.5 g, 1.5 mmol) in dioxane (2 ml) is added dropwise to a stirred solution of sodium sulfite (0.378 g, 3.0 mmol) and sodium hydrogen carbonate (0.252 g, 3.0 mmol) in water at 75° C. After 1 hour at 75° C., bromoacetic acid (0.417 g, 3.0 mmol) is added and heating continued for 1 hour at 100° C. Sodium hydroxide (0.24 g, 6.0 mmol) in water (0.25 ml) is then added and the mixture is heated with stirring at 91° C. for 16 hours. The reaction mixture is allowed to cool, diluted with water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic extracts are washed with brine (75 ml), dried (MgSO4), filtered, and the solvent removed to give the title compound. MH+ 268.9.

Workup

  1. temperatureheating
  2. waitcontinued for 1 hour at 100° C
  3. temperaturethe mixture is heated
  4. temperatureto cool
  5. extractionextracted with dichloromethane (3×75 ml)
  6. washThe combined organic extracts are washed with brine (75 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-fa2f9b6952534fa19dc9cd476fdb7e2c
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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