Sodium Hydroxide → HCID 4577230, compound

HRID 1009462Notes

Reaction equation

HRID 1009462 reaction equation
C([CH:3]([C:23]([OH:25])=[O:24])[N:4]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=1[CH3:22])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])C.[OH-].[Na+]>C(O)C.O1CCOCC1>[Cl:21][C:17]1[C:16]([CH3:22])=[C:15]([N:4]([S:5]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)(=[O:6])=[O:7])[CH2:3][C:23]([OH:25])=[O:24])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67305472HCID 67305472, compound

Product 1

HCID 4577230HCID 4577230, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

35.8 g of ethyl N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycine was dissolved in 157 mL of ethanol and 157 mL of 1,4-dioxane, and 157 mL of a 1 M aqueous sodium hydroxide solution was added thereto, followed by stirring at 60° C. overnight. The reaction liquid was cooled to room temperature, and then concentrated under reduced pressure. The residue was dissolved in water, acidified by addition of 1 M hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 29.3 g of N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycine.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. additionacidified by addition of 1 M hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-82964a38472d43449028ebdc03f2ea19
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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