Phosphorus oxychloride → HCID 86604386, compound

HRID 10111Notes

Reaction equation

HRID 10111 reaction equation
[CH:1]12[CH2:16][CH:12]([CH2:13][NH:14][CH2:15]1)[C:11]1[C:10]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[C:9]3[C:4]([NH:5][C:6](=O)[CH:7]=[CH:8]3)=[CH:3][C:2]2=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:6]1[CH:7]=[CH:8][C:9]2[C:4](=[CH:3][C:2]3[CH:1]4[CH2:16][CH:12]([C:11]=3[C:10]=2[C:17](=[O:22])[C:18]([F:20])([F:19])[F:21])[CH2:13][NH:14][CH2:15]4)[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 692582841-(5,14-Diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,7,9-tetraen-6-one-10-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 86604386HCID 86604386, compound

Conditions

Temperature
100 °C

Procedure

1-(5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,7,9-tetraen-6-one-10-yl)-2,2,2-trifluoro-ethanone (156 mg, 0.49 mmol) was treated with POCl3 (5 mL) and warmed to 100° C. with stirring for 3 hours. After concentration in vacuo, the residue was diluted with CH2Cl2 (15 mL) and carefully treated with saturated NaHCO3 solution (10 mL) with stirring. Once CO2 evolution slowed the mixture was separated and the aqueous layer extracted CH2Cl2 (3 times). The organic layer was washed with H2O and saturated NaCl solution, filtered through cotton and concentrated to a brown oil (217 mg, 93%). (TLC ethyl acetate, Rf 0.3) 1H NMR (400 MHz, 2HCCl3) δ 8.03 (d, J=8.5 Hz, 1H), 7.83 (s, 1H), 7.62 (s, 1H), 7.35 (d, J=8.5 Hz, 1H), 4.43 (m, 1H), 4.01 (m, 1H), 3.62 (m, 1H), 3.29 (m, 2H), 3.23 (m, 1H), 2.45 (m, 1H), 2.10 (d, J=11.6 Hz, 1H). APCI MS m/e 341.1 [(M+1)+].

Workup

  1. concentrationAfter concentration in vacuo
  2. additionthe residue was diluted with CH2Cl2 (15 mL)
  3. additioncarefully treated with saturated NaHCO3 solution (10 mL)
  4. stirringwith stirring
  5. customwas separated
  6. extractionthe aqueous layer extracted CH2Cl2 (3 times)
  7. washThe organic layer was washed with H2O and saturated NaCl solution
  8. filtrationfiltered through cotton
  9. concentrationconcentrated to a brown oil (217 mg, 93%)

Sources & evidence

ORD record
ord-b4d6b3277093439c8ceae4c543cc0e02
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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