Phosphorus oxychloride → HCID 86036623, compound

HRID 2225180Notes

Reaction equation

HRID 2225180 reaction equation
[CH2:1]([C:5]1[N:14]=[C:13](O)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:22])=O>C(Cl)Cl>[CH2:1]([C:5]1[N:14]=[C:13]([Cl:22])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178441852HCID 178441852, compound

Product 1

HCID 86036623HCID 86036623, compoundYield 121.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Preparation D11, Step 2: 2-butyl-6-(trifluoromethyl)-quinazolin-4-ol (100 mg, 0.37 mmol, 1 eq) and phosphorus oxychloride (3.00 mL, 3.22 mmol, 87 eq) were mixed at room temperature under nitrogen then refluxed for 3 hours. The reaction was stripped 3 times from methylene chloride. The residue was dissolved in methylene chloride (25 mL) and rinsed 3 times with saturated sodium bicarbonate (25 mL), 1× with water (25 mL). The organic layer was dried (sodium sulfate) and stripped to give 2-butyl-4-chloro-6-(trifluoromethyl)quinazoline (130 mg) as a tan solid. LCMS of a an analytical sample prepared in MeOH detects (M-Cl+OMe)+=285.24.

Workup

  1. customPreparation D11, Step 2
  2. temperaturethen refluxed for 3 hours
  3. washrinsed 3 times with saturated sodium bicarbonate (25 mL), 1× with water (25 mL)
  4. dry with materialThe organic layer was dried (sodium sulfate)

Sources & evidence

ORD record
ord-59b3496675bd4aa4a4d7d1d488de0083
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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