Triethylamine → HCID 69652716, compound

HRID 1823298Notes

Reaction equation

HRID 1823298 reaction equation
[Cl:1][C:2]1[C:3]([CH:9]=[N:10][OH:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.ClN1C(=O)CCC1=O.[CH2:20]([O:22][C:23](=[O:27])[C:24]#[C:25][CH3:26])[CH3:21].C(N(CC)CC)C>CN(C)C=O.C(OCC)C.O>[CH2:20]([O:22][C:23]([C:24]1[C:9]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=2)=[N:10][O:11][C:25]=1[CH3:26])=[O:27])[CH3:21]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 78043Ethyl 2-butynoateHCID 137193826HCID 137193826, compound

Product 1

HCID 69652716HCID 69652716, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve 3,5-dichloropyridine-2-carboxaldehyde oxime (0.70 g, 0.0037 mol) in N,N-dimethylformamide (10 mL). Add N-chlorosuccinimide (0.55 g, 0.004 mol) in small portions and sitr at ambient temperature until reaction is complete. Pour the mixture into water and extract with ethyl acetate. Wash with water and dry over sodium sulfate. Concentrate in vacuo and use without further purification. Combine this material with ethyl-2-butynoate (6.0 mL, 0.052 mol) under a nitrogen atmosphere. Add triethylamine (3.29 mL, 0.024 mol) in diethyl ether (10 mL) in a dropwise manner and stir overnight at ambient temperature. Quench with water and extract with ethyl acetate. Concentrate and elute over silica gel with dichloromethane to give the desired isoxazole (0.43 g, 39%).

Workup

  1. extractionextract with ethyl acetate
  2. washWash with water
  3. dry with materialdry over sodium sulfate
  4. concentrationConcentrate in vacuo and use without further purification
  5. customQuench with water
  6. extractionextract with ethyl acetate
  7. concentrationConcentrate
  8. washelute over silica gel with dichloromethane

Sources & evidence

ORD record
ord-0d506043fb7e4a538648da1fad5f1400
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

Loading…