Water → HCID 58136407, compound

HRID 877173Notes

Reaction equation

HRID 877173 reaction equation
Br[C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[NH2:9][C:10]1[CH:11]=[C:12]([SH:16])[CH:13]=[CH:14][CH:15]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C>[NH2:9][C:10]1[CH:11]=[C:12]([S:16][C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 315773-AminothiophenolHCID 90097Methyl 2-bromo-2-methylpropionateHCID 516892Sodium Bicarbonate

Product 1

HCID 58136407HCID 58136407, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 1.36 ml (10.5 mmol) of methyl 2-bromo-2-methylpropanoate were added slowly to a solution of 1.2 g (9.6 mmol) of 3-aminobenzenethiol and 1.046 g (12.5 mmol) of sodium bicarbonate in 6 ml of DMF, and the mixture was stirred overnight. After the reaction had ended, the reaction mixture was added to water. The reaction mixture was extracted three times with diethyl ether, and the combined organic phases were washed with saturated sodium chloride solution and dried over magnesium sulfate. After filtration, the solvent was removed to dryness under reduced pressure. This gave 1.45 g (6.4 mmol, 67% of theory) of a colorless solid.

Workup

  1. extractionThe reaction mixture was extracted three times with diethyl ether
  2. washthe combined organic phases were washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was removed to dryness under reduced pressure

Sources & evidence

ORD record
ord-910ebfbc7dbe40fe968abbbe036aeaf4
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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