Thiophenol → HCID 14275569, compound

HRID 867969Notes

Reaction equation

HRID 867969 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5](=[O:9])[O:6][C:7]=1[CH3:8].[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>ClCCl>[CH3:8][C:7]1[O:6][C:5](=[O:9])[O:4][C:3]=1[CH2:2][S:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 98555184-(Chloromethyl)-5-methyl-1,3-dioxol-2-one

Product 1

HCID 14275569HCID 14275569, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 40 ml of dichloromethane was dissolved 2.0 g of 4-chloromethyl-5-methyl-1,3-dioxol-2-one, and 1.5 g of benzenethiol was added. Then, 1.4 g of triethylamine was added, and the mixture was stirred at room temperature for 30 minutes. After the reaction, the solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The insoluble materials were separated by filtration, and the solvent was evaporated under reduced pressure. The residue was subjected to medium-pressure silica gel column chromatography as in Example 1. The eluate was concentrated under reduced pressure to give 2.3 g of the captioned compound as a colorless liquid.

Workup

  1. additionwas added
  2. customAfter the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe insoluble materials were separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f4e9d9b413fb41018cfe2c08d4c5f9b5
Source dataset
uspto-grants-1988_10
Patent number
US04777267

Reaction notes

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