Triethylamine → HCID 20262080, compound

HRID 464555Notes

Reaction equation

HRID 464555 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13](=[CH2:16])[CH2:14][SH:15].C(N(CC)CC)C>O1CCCC1>[CH3:16][C:13](=[CH2:12])[CH2:14][S:15][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 679672,4-DifluoronitrobenzeneHCID 11051576Methallyl mercaptan

Product 1

HCID 20262080HCID 20262080, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.0 g (0.031 mole) of 2,4-difluoronitrobenzene and 2.8 g (0.031 mole) of 2-methyl-2-propenethiol in 25 ml of tetrahydrofuran at room temperature was added dropwise 3.1 g (0.031 mole) of triethylamine. The reaction mixture was stirred at room temperature for forty-eight hours and then at 50° C. for eight hours. The tetrahydrofuran was removed under reduced pressure, and water was mixed with the residue. This aqueous mixture was extracted with chloroform. The chloroform extract was washed with water, dried, and the chloroform evaporated under reduced pressure, leaving an oily residue. Distillation of this residue under reduced pressure yielded 6.0 g of 2-(2-methyl-2-propenylthio)-4-fluoronitrobenzene. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customThe tetrahydrofuran was removed under reduced pressure, and water
  2. additionwas mixed with the residue
  3. extractionThis aqueous mixture was extracted with chloroform
  4. extractionThe chloroform extract
  5. washwas washed with water
  6. customdried
  7. customthe chloroform evaporated under reduced pressure
  8. customleaving an oily residue
  9. distillationDistillation of this residue under reduced pressure

Sources & evidence

ORD record
ord-b717fa2e502249e48bdfc2b1afd2558c
Source dataset
uspto-grants-1985_10
Patent number
US04548640

Reaction notes

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