Dichloromethane → HCID 67818192, compound

HRID 2401432Notes

Reaction equation

HRID 2401432 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]3[C:10]([CH3:11])=[N:9][O:8][C:7]=3[C:12]3([NH:15][C:16](=O)[C:4]=2[CH:3]=1)[CH2:14][CH2:13]3.C(Cl)[Cl:21].P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[Cl:21][C:16]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:19]=[CH:18][C:5]=2[C:6]2[C:10]([CH3:11])=[N:9][O:8][C:7]=2[C:12]2([N:15]=1)[CH2:14][CH2:13]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24819Phosphorus pentachlorideHCID 67817532HCID 67817532, compound

Product 1

HCID 67818192HCID 67818192, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a vial containing 8-chloro-1-methylspiro[benzo[e]isoxazolo[5,4-c]azepine-4,1′-cyclopropan]-6(5H)-one (0.0631 g, 0.230 mmol) was added CH2Cl2 (1 mL). The reaction mixture was heterogeneous and to aid in solubility CHCl3 (0.5 mL) was added. To the homogeneous mixture was added phosphorous pentachloride (0.092 g, 0.442 mmol) in one portion at room temperature. The reaction mixture eventually turned heterogeneous again (˜<10 min) and LC-MS analysis after ˜30 min indicated complete consumption of starting material and formation of desired product. The mixture was diluted with EtOAc and aqueous 10% Na2CO3 (2.8 mL). After initial effervescence, the mixture was stirred for an additional 5-10 min, and the aqueous layer was extracted with EtOAc (3×). The combine organic extracts were washed with water, brine, dried over Na2SO4 and concentrated to give yellow solids. The solids were filtered over a plug of silica and eluted with 30% EtOAc:70% Hexanes. The product 6,8-dichloro-1-methylspiro[benzo[e]isoxazolo[5,4-c]azepine-4,1′-cyclopropane] (61.8 mg, 0.211 mmol, 92% yield) was obtained as off-white solids. LC/MS m/z 293 [M+H]+.

Workup

  1. additionwas added
  2. customconsumption of starting material and formation of desired product
  3. additionThe mixture was diluted with EtOAc and aqueous 10% Na2CO3 (2.8 mL)
  4. extractionthe aqueous layer was extracted with EtOAc (3×)
  5. washThe combine organic extracts were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give yellow solids
  9. filtrationThe solids were filtered over a plug of silica
  10. washeluted with 30% EtOAc

Sources & evidence

ORD record
ord-985cd10fe8a24908aa24d2d6479340d0
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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