Sodium Carbonate → Methyl 3-amino-2-methyl-6-thiocyanatobenzoate

HRID 476530

Reaction equation

HRID 476530 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[S-:13][C:14]#[N:15].[Na+].[Br-].[Na+].BrBr.C(=O)([O-])[O-].[Na+].[Na+]>CO>[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([C:9]([S:13][C:14]#[N:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 24408BromineHCID 253881Sodium BromideHCID 516871Sodium thiocyanateHCID 38010253-Amino-2-methylbenzoic acid methyl ester

Product 1

HCID 14801188Methyl 3-amino-2-methyl-6-thiocyanatobenzoateYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

While maintaining a solution comprising 27.7 g of methyl 3-amino-2-methylbenzoate, 41.5 g of sodium thiocyanate and 250 ml of methanol at a temperature of not higher than 0° C., 100 ml of sodium bromide-saturated methanol with 28.1 g of bromine was slowly dropwise added thereto. The mixture was stirred at room temperature for 3 hours and then poured into 1 liter of ice water. The solution was neutralized with sodium carbonate and then extracted with chloroform. The extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 34.0 g of the desired product as an oily substance.

Workup

  1. temperatureWhile maintaining a solution
  2. customhigher than 0° C.
  3. extractionextracted with chloroform
  4. washThe extract was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-787fce87cce8402592768e9530675cb5
Source dataset
uspto-grants-1989_12
Patent number
US04885022

Linked notes

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