Triethylamine → HCID 178472035, compound

HRID 1517996Notes

Reaction equation

HRID 1517996 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.C[N:18]([CH3:26])[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C.N[CH:35]([OH:37])C>C1(C)C=CC=CC=1.C1COCC1.O.CN(C=O)C>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([C:20](=[CH:19][NH:18][CH2:26][CH2:35][OH:37])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:6]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 522583Acetaldehyde ammoniaHCID 108913672,3-Difluoro-5-iodobenzoic acid

Product 1

HCID 178472035HCID 178472035, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2,3-Difluoro-5-iodobenzoic acid (3.0 g, 10.6 mmol) obtained in Step 1 was dissolved in toluene, and thionyl chloride (3.0 ml, 41.1 mmol) and DMF (catalytic amount) were added. The mixture was heated under reflux for 3 hrs. The reaction solution was concentrated under reduced pressure and THF (15 ml) was added to dissolve the residue. The resulting solution was added dropwise to a solution of ethyl 3-dimethylaminoacrylate (1.66 g, 11.6 mmol) and triethylamine (1.77 ml, 12.7 mmol) in THF (10 ml) and the mixture was stirred with heating at 50° C. for 2.5 hrs. After allowing the mixture to cool, the reaction mixture was filtered and washed with THF (10 ml). Aminoethanol (0.77 ml, 12.7 mmol) was added to the filtrate and the mixture was stirred with heating at 40° C. for 1 hr. After allowing the mixture to cool, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=2:1) to give an object product (3.8 g, yield 85%). of a mixture of E form and Z form as a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. concentrationThe reaction solution was concentrated under reduced pressure and THF (15 ml)
  4. additionwas added
  5. dissolutionto dissolve the residue
  6. temperatureto cool
  7. filtrationthe reaction mixture was filtered
  8. washwashed with THF (10 ml)
  9. stirringthe mixture was stirred
  10. temperaturewith heating at 40° C. for 1 hr
  11. temperatureto cool
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe organic layer was washed with water and saturated brine
  14. dry with materialdried over sodium sulfate
  15. filtrationAfter filtration
  16. concentrationthe filtrate was concentrated under reduced pressure
  17. customthe obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-27e34b90aec1476bb6a733b502c46095
Source dataset
uspto-grants-2012_07
Patent number
US08232401B2

Reaction notes

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