Carbon Tetrachloride → HCID 18925001, compound

HRID 1869100Notes

Reaction equation

HRID 1869100 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17])[N:11]=[CH:10][NH:9][C:8]2=O)([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:40].[C:44]([C:46]1[CH:47]=[C:48]([CH:50]=[CH:51][CH:52]=1)[NH2:49])#[CH:45]>C(O)(C)C>[ClH:40].[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17])[N:11]=[CH:10][N:9]=[C:8]2[NH:49][C:48]1[CH:50]=[CH:51][CH:52]=[C:46]([C:44]#[CH:45])[CH:47]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 104682Benzenamine, 3-ethynyl-HCID 136082989HCID 136082989, compound

Product 1

HCID 18925001HCID 18925001, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6,7-Diisopropoxyquinazolin-4-one (55 mg, 0.210 mmol), triphenylphosphine (121 mg, 0.462 mmol) and 3 mL of carbon tetrachloride were refluxed for 16 hours and the reaction mixture was concentrated in vacuo to a residue which was diluted with 3 mL of isopropyl alcohol and 3-ethynylaniline (30 mg, 0.257 mmol) and refluxed for 3 hours. The cooled reaction mixture was vacuum evaporated to afford the solid title product which was column chromatographed on silica gel eluted with 5% acetone in methylene chloride containing 0.25% triethylamine. Fractions containing the pure product were concentrated in vacuo to a solid which was dissolved in 2 mL of 1N HCl in methanol, precipitated with ethyl ether, filtered and dried in vacuo at 70° C. to afford the title product; 140 mg (75%); mp 241°-242° 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. customevaporated

Sources & evidence

ORD record
ord-0138f487433040d3af4d028108e68de4
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

Loading…