Triethylamine → 4,6-Dichloro-2-(trifluoromethyl)quinazoline

HRID 1391895Notes

Reaction equation

HRID 1391895 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[N:6]=[C:5]2O.P(Cl)(Cl)([Cl:19])=O.C(N(CC)CC)C>C(Cl)Cl>[Cl:19][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178517786HCID 178517786, compound

Product 1

HCID 210882754,6-Dichloro-2-(trifluoromethyl)quinazolineYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Chloro-2-trifluoromethyl-quinazolin-4-ol (1.35 g, 5.43 mmol, 1 eq.), phosphorous oxychloride (4.88 mL, 52.4 mmol, 9.64 eq.) and triethylamine (2.43 mL, 17.4 mmol, 3.21 eq.) were refluxed for 2 hours. Stripped 3× from methylene chloride then dissolved in methylene chloride and rinsed 3× with saturated sodium bicarbonate, 1× with brine. Dried and stripped in vacuo to give an amber oil. Purified over silica gel in 9:1 Hexanes/EtOAc. Obtained 800 mg of off-white solids as product. The product was used immediately in Example 1 Part C.

Workup

  1. washrinsed 3× with saturated sodium bicarbonate, 1× with brine
  2. customDried
  3. customto give an amber oil
  4. customPurified over silica gel in 9:1 Hexanes/EtOAc

Sources & evidence

ORD record
ord-801424aca76b4c8c92feb0b871fda80c
Source dataset
uspto-grants-2008_03
Patent number
US07338947B2

Reaction notes

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