Triethylamine → HCID 13556902, compound

HRID 464554Notes

Reaction equation

HRID 464554 reaction equation
[CH2:1]=[CH:2][CH2:3][SH:4].F[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14].C(N(CC)CC)C>O1CCCC1>[CH2:3]([S:4][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])[CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13367Allyl MercaptanHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 13556902HCID 13556902, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.3 g (0.031 mole) of allylthiol in 25 ml of tetrahydrofuran was added to 5.0 g (0.031 mole) of 2,4-difluoronitrobenzene in 25 ml of tetrahydrofuran at -30° C. To this mixture was added dropwise 3.1 g (0.031 mole) of triethylamine. The temperature was allowed to rise to room temperature and stirring was continued for four hours. The tetrahydrofuran was evaporated under reduced pressure, and water and diethyl ether were added to the residue. The ether layer was separated and dried over anhydrous potassium carbonate. The ether was evaporated under reduced pressure, leaving a liquid residue. This residue was distilled at 105° C./1.2 mm of Hg, yielding 4.2 g of 2-allylthio-4-fluoronitrobenzene. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customto rise to room temperature
  2. customThe tetrahydrofuran was evaporated under reduced pressure, and water and diethyl ether
  3. additionwere added to the residue
  4. customThe ether layer was separated
  5. dry with materialdried over anhydrous potassium carbonate
  6. customThe ether was evaporated under reduced pressure
  7. customleaving a liquid residue
  8. distillationThis residue was distilled at 105° C./1.2 mm of Hg

Sources & evidence

ORD record
ord-7d52994e3a0c4223ab5ad34b2c4316af
Source dataset
uspto-grants-1985_10
Patent number
US04548640

Reaction notes

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