Ethanethiol → Methyl 2-chloro-3-ethylthiomethyl-4-methanesulfonylbenzoate

HRID 1709334Notes

Reaction equation

HRID 1709334 reaction equation
O1CCCC1.[CH2:6]([SH:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[C:18]([Cl:31])=[C:19]([CH:24]=[CH:25][C:26]=1[S:27]([CH3:30])(=[O:29])=[O:28])[C:20]([O:22][CH3:23])=[O:21]>C(Cl)(Cl)Cl>[Cl:31][C:18]1[C:17]([CH2:16][S:8][CH2:6][CH3:7])=[C:26]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

Product 1

HCID 15132839Methyl 2-chloro-3-ethylthiomethyl-4-methanesulfonylbenzoateYield 98.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 100 ml of tetrahydrofuran, 1.3 g of ethanethiol and 1.5 g of potassium carbonate and then 4.4 g of methyl 3-bromomethyl-2-chloro-4-methanesulfonylbenzoate were added, and the mixture was stirred for 1 day at room temperature. Then, the mixture was stirred further for 1 hour at a temperature of from 50° to 60° C. After cooling, chloroform was added thereto, and the mixture was washed with a dilute potassium carbonate aqueous solution. The chloroform layer was separated and dried. Then, the solvent was distilled off to obtain 4.1 g of methyl 2-chloro-3-ethylthiomethyl-4-methanesulfonylbenzoate as an oily substance.

Workup

  1. stirringThen, the mixture was stirred further for 1 hour at a temperature of from 50° to 60° C
  2. temperatureAfter cooling
  3. washthe mixture was washed with a dilute potassium carbonate aqueous solution
  4. customThe chloroform layer was separated
  5. customdried
  6. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-66b1bf08ab00484e9993f77d263bf04c
Source dataset
uspto-grants-1990_08
Patent number
US04948887

Reaction notes

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