Triethylamine → HCID 67270780, compound

HRID 600858Notes

Reaction equation

HRID 600858 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=O.S(Cl)(Cl)=O.[CH3:17][N:18]([CH3:26])[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C>C1(C)C=CC=CC=1.O1CCCC1.CCCCCC.CN(C)C=O>[F:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([C:20](=[CH:19][N:18]([CH3:26])[CH3:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:6]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 17857039HCID 17857039, compound

Product 1

HCID 67270780HCID 67270780, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Difluoro-3-methylbenzoate (4.97 g, 28.9 mmol) was dissolved in toluene (50 ml), and after adding N,N-dimethylformamide (0.1 ml) and thionyl chloride (3.16 ml, 43.4 mmol) thereto, it was stirred for 14 hours in an oil bath of 80° C. The reaction solution was then cooled and thereafter concentrated under a reduced pressure. After adding toluene to the residue and repeating concentration under a reduced pressure, the residue obtained was dissolved in tetrahydrofuran (10 ml). This solution was added dropwise while cooling with ice to a solution in which ethyl 3-dimethylaminoacrylate (4.97 g, 34.7 mmol) and triethylamine (5.04 ml, 36.1 mmol) were dissolved in tetrahydrofuran (20 ml). After completion of dripping, the reaction solution was heated under reflux for 10 hours. After completion of the reaction, the reaction solution was filtered, the triethylamine hydrochloride salt was removed (by diethyl ether washing), and the filtrate was concentrated under a reduced pressure. The residue obtained was applied to a short silica gel chromatography and 6.70 g (78%) of the title compound was obtained in the form of a yellow powder from an n-hexane:ethyl acetate=1:1 eluate.

Workup

  1. temperatureThe reaction solution was then cooled
  2. concentrationconcentrated under a reduced pressure
  3. additionAfter adding toluene
  4. concentrationto the residue and repeating concentration under a reduced pressure
  5. customthe residue obtained
  6. additionThis solution was added dropwise
  7. temperaturethe reaction solution was heated
  8. temperatureunder reflux for 10 hours
  9. customAfter completion of the reaction
  10. filtrationthe reaction solution was filtered
  11. customthe triethylamine hydrochloride salt was removed (by diethyl ether washing)
  12. concentrationthe filtrate was concentrated under a reduced pressure
  13. customThe residue obtained

Sources & evidence

ORD record
ord-31346111ea904f6e81caa210562ede17
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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