Potassium Hydroxide → HCID 19814654, compound

HRID 466742

Reaction equation

HRID 466742 reaction equation
[OH-].[K+].[OH:3][C:4]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[CH3:15][N:16]([CH3:20])[C:17](Cl)=[S:18]>CO>[CH3:15][N:16]([C:17](=[S:18])[O:3][C:4]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH3:20]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 27871Dimethylthiocarbamoyl chlorideHCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

Product 1

HCID 19814654HCID 19814654, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 12 g of KOH pellets, 150 mL of methanol and 24.9 g of methyl 2-hydroxy-3-methylbenzoate (I) was stirred at room temperature for 0.5 hours. The mixture was then cooled to 5° C. and 19 g of dimethylthiocarbamoyl chloride was added in one portion. An exotherm of 5° C. was observed. The resulting mixture was stirred for 2 hours and then added to 300 mL of ice water. After filtering, the crystalline product was washed with water and oven dried to yield 30-35 g of methyl 2-[(dimethyl-amino)thioxomethoxy]-3-methylbenzoate II, (E is O, W is S) in 80-92% yield, mp 94-96° C.

Workup

  1. temperatureThe mixture was then cooled to 5° C.
  2. customAn exotherm of 5° C.
  3. stirringThe resulting mixture was stirred for 2 hours
  4. filtrationAfter filtering
  5. washthe crystalline product was washed with water and oven
  6. customdried

Sources & evidence

ORD record
ord-3174f41418564e6594da6e392c8d9c9a
Source dataset
uspto-grants-1992_10
Patent number
US05157119

Linked notes

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