Triethylamine → HCID 14275572, compound

HRID 867970Notes

Reaction equation

HRID 867970 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5](=[O:9])[O:6][C:7]=1[CH3:8].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH2:2][C:3]2[O:4][C:5](=[O:9])[O:6][C:7]=2[CH3:8])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127654-MethoxybenzenethiolHCID 98555184-(Chloromethyl)-5-methyl-1,3-dioxol-2-one

Product 1

HCID 14275572HCID 14275572, compoundYield 67.7%

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 1.9 g of 4-methoxybenzenethiol 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. 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 evaporated under reduced pressure, and the residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane to give 2.3 g of the captioned compound as pale yellow crystals.

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. customThe eluate was evaporated under reduced pressure
  8. customthe residue was recrystallized from a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-f29697fd1f0541d893de3d9c0750e301
Source dataset
uspto-grants-1988_10
Patent number
US04777267

Reaction notes

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