4-Aminobenzoic Acid → HCID 57663055, compound

HRID 406847Notes

Reaction equation

HRID 406847 reaction equation
[CH:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9](=O)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[NH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(O)CCC>[CH:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([NH:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178517434HCID 178517434, compound

Product 1

HCID 57663055HCID 57663055, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-cyclohexylquinazolin-2(1H)-one (500 mg, 2.2 mmol) and phosphorous oxychloride (10 mL, 111 mmol) was heated to reflux for 1 h. The volatiles were removed under reduced pressure, and then the residue was treated with ice water and extracted with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride and dried over sodium sulfate. The solvent was removed on a rotary evaporator, and to this residue was added 4-aminobenzoic acid (300 mg, 2.2 mmol), triethylamine (435 μL, 3.0 mmol) and n-butanol (5 mL). This mixture was heated to 140° C. for 25 min. The mixture was cooled to rt and triturated with ether. The residual solid was collected via vacuum filtration, washed with ether and dried to afford 4-(4-cyclohexylquinazolin-2-ylamino)benzoic acid (370 mg, 48%) as an off white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. customThe volatiles were removed under reduced pressure
  4. additionthe residue was treated with ice water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with saturated sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed on a rotary evaporator
  9. temperatureThe mixture was cooled to rt
  10. customtriturated with ether
  11. filtrationThe residual solid was collected via vacuum filtration
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-b94e1d8fb94a40ec8fbc233afde841ed
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Reaction notes

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