Hydrochloric Acid → HCID 18925082, compound

HRID 1288893Notes

Reaction equation

HRID 1288893 reaction equation
[CH2:1]([S:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=O)[NH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:35]([C:37]1[CH:38]=[C:39]([CH:41]=[CH:42][CH:43]=1)[NH2:40])#[CH:36].[ClH:44]>C(O)(C)C.CO.C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[ClH:44].[CH2:1]([S:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:40][C:39]3[CH:41]=[CH:42][CH:43]=[C:37]([C:35]#[CH:36])[CH:38]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 104682Benzenamine, 3-ethynyl-HCID 136018506HCID 136018506, compound

Product 1

HCID 18925082HCID 18925082, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

7-Propylsulfanyl-quinazolin-4-one (300 mg, 1.36 mmol), triphenylphosphine (785 mg, 2.99 mmol), 1.31 mL of carbon tetrachloride and 5 mL of chloroform were refluxed for 16 hours and the reaction mixture was concentrated in vacuo to a residue which was diluted with 5 mL of isopropyl alcohol and 3-ethynylaniline (175 mg, 1.49 mmol) and refluxed for 3 hours. The cooled reaction mixture was concentrated in vacuo and the residue purified by column chromatography on silica gel eluted with 10% methanol in chloroform. Fractions containing the pure title product, as the frree amine, were concentrated in vacuo to afford solid which was added to 3 mL of 1N HCl in methanol. This solution was evaporated in vacuo to a residue which was triturated with 4 mL of hot isopropyl alcohol cooled and filtered. The solid thus obtained was dried in vacuo at 70° C. to afford pure title product; 239 mg (55%); mp 229°-230° C.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo to a residue which
  2. temperaturerefluxed for 3 hours
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customthe residue purified by column chromatography on silica gel
  6. washeluted with 10% methanol in chloroform
  7. additionFractions containing the pure title product
  8. concentrationas the frree amine, were concentrated in vacuo
  9. customto afford solid which
  10. customThis solution was evaporated in vacuo to a residue which
  11. customwas triturated with 4 mL of hot isopropyl alcohol
  12. temperaturecooled
  13. filtrationfiltered
  14. customThe solid thus obtained
  15. customwas dried in vacuo at 70° C.

Sources & evidence

ORD record
ord-25f61556128a4163bf7796a4ad18c87c
Source dataset
uspto-grants-1998_05
Patent number
US05747498

Reaction notes

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