tert-Butyl mercaptan → HCID 13472263, compound

HRID 483058Notes

Reaction equation

HRID 483058 reaction equation
C[O-].[Na+].[CH3:4][C:5]([CH3:8])([SH:7])[CH3:6].Br[CH2:10][C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]>CO>[CH3:4][C:5]([CH3:8])([S:7][CH2:10][C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14])[CH3:6]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 13472263HCID 13472263, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 34.7 g of sodium methoxide in 600 ml methanol was added 57.9 g of 1,1-dimethylethanethiol below 25°. The resulting solution was stirred one hour before the portionwise addition of 172.7 g of methyl 2-bromomethyl-3-nitrobenzoate. The resulting suspension was refluxed two hours. The mixture was cooled, and the solvent evaporated in vacuo. The residual oil was partitioned between ether and water. The organic solution was washed twice with 2.5% sodium hydroxide solution, twice with water, followed by brine, then dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo to give 164.2 g of crude methyl 2-[(1,1-dimethylethylthio)methyl]-3-nitrobenzoate as an oil.

Workup

  1. temperatureThe resulting suspension was refluxed two hours
  2. temperatureThe mixture was cooled
  3. customthe solvent evaporated in vacuo
  4. customThe residual oil was partitioned between ether and water
  5. washThe organic solution was washed twice with 2.5% sodium hydroxide solution, twice with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5c0e70c2b7b34fe28355e6c82a1301cf
Source dataset
uspto-grants-1986_03
Patent number
US04578108

Reaction notes

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