Phosphorus pentachloride → HCID 86693068, compound

HRID 575036Notes

Reaction equation

HRID 575036 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:14][CH:8]([NH:9][C:10]2=O)[CH2:7]3)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:16].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:14][CH:8]([N:9]=[C:10]2[Cl:16])[CH2:7]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 81531DiisopropylethylamineHCID 866930661451085-14-5

Product 1

HCID 86693068HCID 86693068, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

Into a 5000-mL 3-necked round-bottom flask was placed 5-bromo-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6-trien-8-one (223 g, 884.55 mmol, 1.00 equiv), PhCH3 (3500 mL), PCl5 (560 g, 2.69 mol, 3.00 equiv), and DIPEA (275 g, 3.00 equiv). The resulting solution was stirred at 85° C. for 5 h and quenched by the addition of 300 g of DIPEA. The solids were filtered out and the filtrate was concentrated under vacuum to afford 260 g (crude) of 5-bromo-8-chloro-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6,8-tetraene as a black oil.

Workup

  1. customInto a 5000-mL 3-necked round-bottom flask was placed
  2. customquenched by the addition of 300 g of DIPEA
  3. filtrationThe solids were filtered out
  4. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4cc4af2f3da04349abcd7dab760f2076
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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