Sodium Hydroxide → HCID 1652752, compound

HRID 1642123Notes

Reaction equation

HRID 1642123 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18]C)=[O:17])[CH3:13])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].CO.O1CCOCC1.[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([OH:18])=[O:17])[CH3:13])(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21966525Dioxane MethanolHCID 66755893HCID 66755893, compound

Product 1

HCID 1652752HCID 1652752, compound

Procedure

Methyl 2-(3,4-dichloro-N-methylphenylsulfonamido)benzoate (21.0 g, 56.1 mmol) was dissolved in a mixture of methanol/dioxane/4 M NaOH (15/4/1, 420 ml, 84 mmol NaOH, 1.5 eq.), and further 4 M NaOH (63 ml, 252 mmol, 4.5 eq.) was added. The solution was stirred overnight at room temperature and then concentrated using a rotary evaporator. Ethyl acetate (800 ml) was added to the residue, and the mixture was washed with 0.5 M KHSO4 (1000 ml). The aqueous phase was then extracted three times with ethyl acetate (350 ml each time), and the combined organic phases were washed with saturated NaCl solution (500 ml). The organic phase was dried (sodium sulfate) and concentrated in vacuo.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customa rotary evaporator
  4. additionEthyl acetate (800 ml) was added to the residue
  5. washthe mixture was washed with 0.5 M KHSO4 (1000 ml)
  6. extractionThe aqueous phase was then extracted three times with ethyl acetate (350 ml each time)
  7. washthe combined organic phases were washed with saturated NaCl solution (500 ml)
  8. dry with materialThe organic phase was dried (sodium sulfate)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f786b27f2da24c46a916f6e31e7bbcb7
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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