Potassium Carbonate → HCID 13006791, compound

HRID 1250423Notes

Reaction equation

HRID 1250423 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>CC(C)=O.ClCCl>[CH3:24][S:25]([O:17][C:14]1[CH:15]=[CH:16][C:11]([S:10][CH2:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:7][CH:6]=2)=[CH:12][CH:13]=1)(=[O:27])=[O:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 147940714,4'-(Methylenedisulfanediyl)diphenol

Product 1

HCID 13006791HCID 13006791, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

In 200 g of acetone was dissolved 23 g (0.1 mol) of the bis(4-hydroxyphenylthio)methane crude product in Synthesis Example 1. To this were added 35 g (0.25 mol) of potassium carbonate and 28 g (0.24 mol) of methanesulfonylchloride. While refluxing in an oil bath at 70° C., the solution was ripened for 4 hours. After cooling, the inorganic salt was filtered and washed with 50 g of acetone. The filtrate and wash liquid combined was concentrated, yielding an oily product, which was dissolved in 150 g of dichloromethane. This solution was washed with 100 g of water, and concentrated again. There was yielded 38 g of a concentrated oily residue, which was used in the subsequent reaction without further purification. It is noted that this oily matter crystallized when kept at room temperature.

Workup

  1. customin Synthesis Example 1
  2. temperatureAfter cooling
  3. filtrationthe inorganic salt was filtered
  4. washwashed with 50 g of acetone
  5. washThe filtrate and wash liquid
  6. concentrationcombined was concentrated
  7. customyielding an oily product, which
  8. washThis solution was washed with 100 g of water
  9. concentrationconcentrated again

Sources & evidence

ORD record
ord-23983aea9d774ac9a3ecb742ee73998d
Source dataset
uspto-grants-2002_01
Patent number
US06338931B1

Reaction notes

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