Phosphorus oxychloride → HCID 57707853, compound

HRID 1397805Notes

Reaction equation

HRID 1397805 reaction equation
[CH3:1][C:2]1[C:3](O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]([F:15])([F:14])[F:13].P(Cl)(Cl)([Cl:19])=O>[NH4+].[OH-]>[Cl:19][C:3]1[C:2]([CH3:1])=[N:11][C:10]2[C:5]([N:4]=1)=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178432148HCID 178432148, compound

Product 1

HCID 57707853HCID 57707853, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-methyl-8-(trifluoromethyl)quinoxalin-2-ol (0.8292 g, 3.634 mmol) and phosphorous oxychloride (6.653 mL, 72.68 mmol) was stirred at 100° C. After 1.5 h, the mixture was cooled to room temperature. The mixture was poured into ice (˜50 mL) with stirring and neutralized with NH4OH (30 mL) and ice with stirring. The resulting precipitate was collected by filtration, rinsed with water (100 mL), and dried to give 3-chloro-2-methyl-5-(trifluoromethyl)-quinoxaline as a pink solid: 1H NMR (400 MHz, DMF) 8 ppm 8.35 (1 H, d, J=8.4 Hz), 8.25 (1 H, d, J=7.4 Hz), 7.94-8.02 (1 H, m), 2.80 (3 H, s); LC-MS (ESI) m/z 247.0 [M+H]+. The pink solid was carried on crude without purification for the next step.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. stirringwith stirring
  3. stirringwith stirring
  4. filtrationThe resulting precipitate was collected by filtration
  5. washrinsed with water (100 mL)
  6. customdried

Sources & evidence

ORD record
ord-f3ecd524a1444884a0a0b875bf90719f
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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