Water → 4-Ethylthio-5-methyl-6-ethoxycarbonyl-8-chlorothiochroman

HRID 1275462Notes

Reaction equation

HRID 1275462 reaction equation
Cl[CH:2]1[C:11]2[C:6](=[C:7]([Cl:18])[CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=2[CH3:12])[S:5][CH2:4][CH2:3]1.[CH2:19]([SH:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:19]([S:21][CH:2]1[C:11]2[C:6](=[C:7]([Cl:18])[CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=2[CH3:12])[S:5][CH2:4][CH2:3]1)[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 221183894,8-Dichloro-5-methyl-6-ethoxycarbonylthiochroman

Product 1

HCID 221184604-Ethylthio-5-methyl-6-ethoxycarbonyl-8-chlorothiochromanYield 139.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.8 Gram (2.6 mmol) of 4,8-dichloro-5-methyl-6-ethoxycarbonylthiochroman was dissolved in 5 ml of N,N-dimethylformamide, and 0.15 ml (3.1 mmol) of ethanethiol and 0.43 g (3.1 mmol) of potassium carbonate were added. The mixture was stirred at room temperature for 2 days. After the completion of the reaction, 20 ml of water was added, and the reaction mixture was extracted with ethyl acetate twice. An organic layer was washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 1.2 g (yield 100%) of 4-ethylthio-5-methyl-6-ethoxycarbonyl-8-chlorothiochroman.

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with ethyl acetate twice
  3. washAn organic layer was washed with water and with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-45552dfeec094c4b80d0b9b39424fe67
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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