Phosphorus pentachloride → HCID 67812971, compound

HRID 2401394Notes

Reaction equation

HRID 2401394 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[C:9](=O)[NH:10][CH:11]([C:12]([F:15])([F:14])[F:13])[C:5]=2[O:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:22]>C(Cl)Cl>[Cl:22][C:9]1[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH:11]([C:12]([F:15])([F:14])[F:13])[N:10]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachloride2×HCID 67815309HCID 67815309, compound

Product 1

HCID 67812971HCID 67812971, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask was added 1-methyl-4-(trifluoromethyl)-4H-benzo[c]isoxazolo[4,5-e]azepin-6(5H)-one (86 mg, 0.305 mmol), DCM (2 mL), and PCl5 (102 mg, 0.488 mmol). The solution was stirred at room temperature for 30 min before addition of more PCl5 (˜0.5 eq). The solution was stirred at room temperature for 4 h before pouring onto an ice-saturated aqueous NaHCO3 mixture. The layers were separated and the aqueous phase was extracted with DCM. The combined organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford the titled compound (52.9 mg, 0.176 mmol). LC/MS m/z 301 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-8ee6782b5ac14b85853f36a1e5f6376f
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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