Water → Methyl 3-amino-2-methyl-6-methylthiobenzoate

HRID 476531Notes

Reaction equation

HRID 476531 reaction equation
O.O.O.O.O.O.O.O.O.[S-2:10].[Na+].[Na+].O.[NH2:14][C:15]1[C:16]([CH3:28])=[C:17]([C:22](SC#N)=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=O.[CH3:29]I>C(O)C>[NH2:14][C:15]1[C:16]([CH3:28])=[C:17]([C:22]([CH3:29])=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[S:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 73972Sodium sulfide nonahydrateHCID 14801188Methyl 3-amino-2-methyl-6-thiocyanatobenzoate

Product 1

HCID 54391819Methyl 3-amino-2-methyl-6-methylthiobenzoateYield 104.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution comprising 39.5 g of sodium sulfide nonahydrate and 110 ml of water, a solution comprising 32.9 g of methyl 3-amino-2-methyl-6-thiocyanobenzoate and 300 ml of ethanol was dropwise added. The mixture was stirred at room temperature for 1.5 hours, and 24.0 g of methyl iodide was dropwise added under cooling with ice. The mixture was stirred further at room temperature for 2 hours and then concentrated under reduced pressure. A saturated sodium chloride aqueous solution was added thereto, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 30.1 g of the desired product as an oily substance.

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice
  3. stirringThe mixture was stirred further at room temperature for 2 hours
  4. concentrationconcentrated under reduced pressure
  5. additionA saturated sodium chloride aqueous solution was added
  6. extractionthe mixture was extracted with chloroform
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-7b4cd22ca44b4f05976d167bcba2c59c
Source dataset
uspto-grants-1989_12
Patent number
US04885022

Reaction notes

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