Phosphorus oxychloride → HCID 57958802, compound

HRID 1187268Notes

Reaction equation

HRID 1187268 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.O=P(Cl)(Cl)[Cl:30]>C1(C)C=CC=CC=1>[Cl:30][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178517960HCID 178517960, compound

Product 1

HCID 57958802HCID 57958802, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 4-hydroxy-6-(4-fluorophenyl)-quinazoline (720 mg, 3 mmol) in toluene (20 ml) was added diisopropylethylamine (1.5 ml, 9 mmol) and POCl3 (0.84 ml, 9 mmol). The mixture was refluxed for 1 hour. The solvents were evaporated in vacuo. The residue was redissolved in dichloromethane and the organic layer was washed with ice water till pH 6-7. The combined organic layers were dried over MgSO4 and concentrated to yield the title compound as a yellow solid (700 mg, yield: 90%) was characterized by its mass spectrum as follows: MS (m/z): 259 ([M+H]+, 100).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customThe solvents were evaporated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washthe organic layer was washed with ice water till pH 6-7
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aec81a2c8714424bae36776e74199166
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

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