Triethylamine → HCID 14275577, compound

HRID 867973Notes

Reaction equation

HRID 867973 reaction equation
Br[CH2:2][C:3]1[O:4][C:5](=[O:8])[O:6][CH:7]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1)([O-:11])=[O:10].C(N(CC)CC)C>ClCCl>[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH2:2][C:3]2[O:4][C:5](=[O:8])[O:6][CH:7]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 158094-NitrobenzenethiolHCID 12832615HCID 12832615, compound

Product 1

HCID 14275577HCID 14275577, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 30 ml of dichloromethane was dissolved 1.0 g of 4-bromomethyl-1,3-dioxol-2-one, and 0.9 g of 4-nitrobenzenethiol was added. Then, 0.6 g of triethylamine was added, and the mixture was stirred at room temperature for 1 hour. 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 [except that the column was eluted with a mixture of chloroform and n-hexane (2/1, v/v)]. The eluate was evaporated under reduced pressure, and the residue was recrystallized from a mixed solvent of chloroform and n-hexane to give 0.5 g of the captioned compound as 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. washwas eluted with a mixture of chloroform and n-hexane (2/1
  8. customThe eluate was evaporated under reduced pressure
  9. customthe residue was recrystallized from a mixed solvent of chloroform and n-hexane

Sources & evidence

ORD record
ord-3ee44317c9054ff88ad8d0e7c9714ef5
Source dataset
uspto-grants-1988_10
Patent number
US04777267

Reaction notes

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