Sodium Hydroxide → HCID 12138351, compound

HRID 987176Notes

Reaction equation

HRID 987176 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]([S:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([S:16][C:17](=[O:21])[N:18]([CH3:20])[CH3:19])[CH:15]=1)[C:9]([O:11]C)=[O:10])=[O:4].[OH-].[Na+]>>[CH3:1][N:2]([CH3:22])[C:3]([S:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([S:16][C:17](=[O:21])[N:18]([CH3:20])[CH3:19])[CH:15]=1)[C:9]([OH:11])=[O:10])=[O:4]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 12138342Methyl 3,5-bis(dimethylcarbamoylthio)benzoate

Product 1

HCID 12138351HCID 12138351, compoundYield 87.2%

Procedure

Methyl 3,5-bis(dimethylcarbamoylthio)benzoate (3.42 g, 10 mmol) was made to react with 5% aqueous sodium hydroxide solution (10 ml. 12.5 mmol) for 3 hours at 22-25° C. with stirring. After cooling by the addition of 50 ml of ice-water, the reaction mixture was extracted with ethyl acetate (300 ml×3) and the extract was dried over magnesium sulfate. The ethyl acetate was evaporated under reduced pressure and the colorless crystals thus obtained was recrystallized from ethanol to give 2.86 g (87.2%) of 3,5-bis(dimethylcarbamoylthio)benzoic acid as colorless needles. The melting point is 196-198° C. (with decomposition).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (300 ml×3)
  2. dry with materialthe extract was dried over magnesium sulfate
  3. customThe ethyl acetate was evaporated under reduced pressure
  4. customthe colorless crystals thus obtained
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-53656245d6054e1486b8d8e47cd86770
Source dataset
uspto-grants-2003_10
Patent number
US06630578B2

Reaction notes

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